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Interesting. I've been working on http://tiemonster.com/ for 2 months now which is similar, but focuses solely on ties.
I thought the idea was interesting so I followed the link to your site. From the tag line, I initially thought that this was going to cost me $18 every month. It was only after reading the other text on that page that I realised that it's a once a month opt in.
Thanks for the input: I should make that more clear. It was originally going to be $18/month, but the more I thought about it, the more I realized that I wouldn't want it that way if I were the customer.

Every month, you get an email with pics of 2-4 different ties. If you like one, you order it. If you don't, you don't order it.

Where do I get in line to be an early customer? Is there a "let me know when you go live" sign up page?

And actually, I LOVE to shop. I just have no taste for clothes. I wouldn't know how to define my style. I need help.

Ditto this. A curse of being a nerdy comparative shopper and having little sense of clothing style makes this a got-to-have service.
Yes, I'd love to hear when the site launches too.
Guys don't hate to shop, we just go to the store already knowing what we're there to get.
I think there's "shopping" (going in to a store to purchase something) then there's "shopping" (browsing, learning, touching, comparing, deciding, etc).

I don't know many guys who like to shop (the second meaning) for clothing, but don't mind purchasing them (going in to a store, finding the item, paying for it, then leaving).

"I think there's "shopping" (going in to a store to purchase something) then there's "shopping" (browsing, learning, touching, comparing, deciding, etc)."

Shopping vs. Browsing, then would be more fitting?

I don't like either one of them. As for the first kind, I don't even know what to look for; there is too much choice. I also hate trying things on in the store. And the second kind of shopping I simply don't have the energy or motivation for.

I'm still waiting for a gizmo that does a 3d scan of me and automagically finds the best fitting clothes, shoes, etc online :)

Not always, I must have spent at least 30 seconds choosing a new shirt at lunchtime.
Yep, that's exactly it : the difference between men and women - or at least me and my girlfriend, to avoid generalization :) - is that we know what and where to buy what we need.

When she goes out 'shopping', it defines a hobby, whereas it defines an concrete action for men. At least I guess :) (please don't call me macho !)

There's a startup in France doing that : http://dress-me.fr/beta They are polishing the beta, but the app is pretty solid. On wider range, social shopping and social fashion have been really hot lately, and over the past 2 years.

I've worked on http://styyler.com for some time (never finalized it), and we were inspired by the fashism.com, polyvore.com ($8M funding), chictopia.com, lookbook.nu, weardrobe.com (acquired by Like.com), chicisimo.com, ...

Love the links and too funny there is one in France with a similar name. What is interesting is only focused on women.
I'm one of those hate-shopping because I don't really understand style. It's just not part of my mental domain.

To "figure out what their style is" is really the missing link for me, and I'd probably pay for this alone. However, I at least have some interest in it, just because my brother is a complete 180 from me and is very into style/clothing.

One cautionary note, the target has to recognize the need for the service, which might make it a harder sell. Look at how hard it is to get people to do something about finances! It's simply a blind spot for many, in the same way style is. Those hate to shop folks don't see why we should care about it. What's the benefit?

If I was at all style conscious I'd be more inclined to focus on the opinions and suggestions feature, even though it seems like an afterthought to your feature set. People who 'get' style and the clueless would both benefit (and frankly, the in style people are going to be more passionate about it).

Interesting, I love hearing about shopping options for men! There are too few options for us out there, but that's both a blessing and a curse. If you're savvy, it can save you time. Women have more options, but they also have more to sift through. Men can be incredibly efficient by comparison, just because we have less to go through and the good stuff is easier to spot.

In the last year I managed to transform my wardrobe from jeans + threadless shirts to strictly dress clothes, but without looking conventional about it or spending a lot. It took some work initially, and some courage to try things out of my comfort zone, but now I dress well by default and it feels good!

First place I go is Value Village or another used clothing shop, maybe once every couple weeks. I don't spend more than 5 minutes (you learn to be efficient pretty quickly). I look at dress shirts, pants, jackets, and ties. Nothing else. I may not find anything, but I feel good when I do ($5-10/shirt, heck yes!). I've found several great shirts that would be $60+ new, and a couple really sweet blazers too.

Then I hit somewhere like Winners, reasonably stylish but not so expensive. When I find something I think I like, I ask myself a couple questions:

a) Does it look like a "dad" shirt/pant? b) Would a teenager wear it?

Both are deal-breakers. If I'm really unsure if it's too loud, I'll try it anyway. But be strict on fit. Dress shirts that look like a garbage bag wrapped around your waist are terrible. Of course, you have to tweak to your physical size, but you can find things that flatter. If it doesn't flatter, even if it's nice, put it back (even if it's "your size").

And for the first while, have a woman come with you, but tell her what you're going for. She'll steer you away from the truly awful, but encourage you to take a chance on the brilliant too :)

This is a promising market if other outfits like http://www.trunkclub.com/ and http://manpacks.com/ are any indication.

I think the trick, though, is making sure that you can align style with your customer. When i first saw trunkclub i thought "netflix for clothes" which is a pretty novel concept if you figure that reselling overstock, late season purchases ala http://gilt.com/ is a pretty solid concept but if you also add-in the whole "personalized wardrobe" aspect, then it's really something exciting for folks that want nice wardrobe standards similar to what jesse at http://putthison.com/ advocates but don't need it this season.

Never heard of Trunk Club, but I love the execution. The interesting thing I'm taking away as a point of comparison is how superior an identity like "Trunk Club" is versus a simple "I found a clever domain that was available" type identity like dress.me.

"Dress Me" is kind of immasculating/infantilizing, whereas Trunk Club is kind of exclusive and sort of has an old world sophistication to it, both in use of throwback terminology "trunk" and the fact that clubs are such "guy things."

Not really comparing the feasibility of one business or the other, just pointing out my reaction to the identities...

One thing that has kept me away from Man Packs is that I have no idea how often I need new socks, underwear, or shaving cream. I'd love to have them sent to me automatically when I'm in need, but it's hard to put that on a schedule. It's probably close to once a year - but it's far enough apart that I don't really know how often I really need them.

Dress.me sounds like a better execution for my preferences - I need a new shirt and some new jeans, so I go to the website and it finds exactly the right items for me with minimal effort or decision making on my part.

Trunk Club is exactly how I would of expected Dress.me to work if I were signing up. I think just recommending doesn't go far enough. Getting a box in the mail with everything put together for you seems much nicer.

Having a personal shopper is appealing I think. That being said, their brands are definitely on the higher end and more than what I'd probably be willing to spend on clothes. E.G. Denim ranging from $165 - $225 means a single outfit could get pretty expensive quick.

Still, I can definitely see the high end of the market being viable though. Seems like demand would exist at mid-market prices though too.

If you love a DVD you got from Netflix, you still put it in the envelope and send it back for a replacement. That's where all of these clothing services fall short. If I keep the clothing I like, I end up with a pile of dirty clothing (that I like). Let me return it all, check a box indicating what I liked, then send me a clean but comparable replacement. Heck, if you follow the Netflix model and let me browse styles online, I'll be able to fine-tune my tastes in no time, without the help of any fashion consultant. As a man, I don't mind shopping, but I'm frustrated when I'm confronted with swimsuits on a day I want to buy a turtleneck, and laundry's a chore. An online closet would solve a number of headaches for a lot of men.
I rather suspect the segment of people who would rather ship dirty laundry via UPS and have it replaced with different clothing rather than just doing their laundry is comparatively small. The people who can afford such a luxury can generally afford to have a washer and dryer in their residence, or at least a straight-up laundry service.

Also, your idea would require used clothing to be laundered and shipped out to other customers. There's probably room for an online Goodwill, but that's literally what it would have to be.

Just for idle speculation: what options does the HN crowd think there are for monetizing a service like this?

Charging a monthly fee for access to the service, or a fee for each consultation? Some sort of referral fee or commission scheme for referring customer to the (eventual) brands and stores?

Finding clothes that fit is an important part of looking nice/stylish. It's also a serious hurdle to shopping online and why I never do it. I think a service like dress.me will need to address this in some way or the process will remain somewhat anxiety-laden.
Or it just needs effortless returns, like Zappos or WarbyParker.com
Returns are always a pain in the butt. No matter how easy you make it sound, people are going to be anxious about it. But even assuming returns are effortless, they're a HUGE money sinkhole for online retailers (Zappos returns average 35%).
Do you have a link for the return rate? Not that I doubt you, but it'd be some great data to have.
And a huge time sinkhole for me. I have a few tshirts that don't fit very well and didn't bother returning because I didn't want to take the time to go to the post office and wait for the package to come back.
That works for things like shoes and t-shirts, but not trousers and regular shirts. It sends a bad sartorial signal to tell people just to slap on something with a decent-ish fit.

It's fine for a shop, but bad for something aimed at dressing people properly and teaching them how to do so themselves.

As a shop, it would be really cool to commission a set of really cheap "try-me-ons" in every size. You could then send these out to people for free with a prepaid return envelope - very much like online jewellers will send you a paper ring sizer for free. Just have people input what they reckon their size is, and send them that plus two sizes on either side. Make them as plain, cheap and flimsy as possible - cheaper postage, people don't order them as free clothing ('Unlimited supplies of plain white tees? Yes please!'), and if you don't get them back it doesn't cost too much.

Unfortunately, due to the differences in sizing between manufacturers, you'd probably have to be commissioning your own products for this to work, but it would be very cool for an off-the-peg suit shop, medium-high end lifestyle catalog (Land's End, etc) or something similar.

You may need fitting guides to show people how particular pieces of clothing should fit (trouser crease should break just above the shoe, shoulders should fit without bulging or sagging...) For bonus points, produce them with several different models with different body sizes - for me, having a heavier guy modelling a suit and showing how well it can disguise a gut would be a major selling point :)

Except that fit is often dependent on style. I have clothes in the same category but different styles from the same retailer where I need different sizes; heck, occasionally I've ended up having to compare different copies of the same garment in the same size, because copy variation made a worthwhile difference to fit. OK, maybe I'm a picky guy with my wardrobe ;-)

Shoes, speaking personally, would be a total non-starter online. I seem to have narrower heels than many; I'll routinely find myself searching styles to find the ones that fit me properly there rather than slipping, even if they're right elsewhere. I'm sure some others will be a little wide acrosss the toes and need just the right level of bulging across the front, or a different arch height that makes positioning of the insole's mound under the bridge or the tongue important for their comfort.

tl;dr: I can't always just buy a certain size and know that will be right. If your business model is dependent on that being possible, it won't work for me and I doubt I'm unique.

Yes, that's definitely true. Never thought of trying different instances of the same size and same style myself, actually... it's often hard enough to find a single instance!

Perhaps what we just need is rapid prototyping for clothes: "I'd like one like this, but with a more generous waist". Like bespoke tailoring but cheap and quick.

Never thought of trying different instances of the same size and same style myself, actually... it's often hard enough to find a single instance!

Agreed. It's not something I've done very often, but (for example) when you notice that the same trousers in two different waist sizes has different leg lengths in spite of what the tickets say, it's worth checking another pair sometimes.

For you, maybe shoes online are a non-starter. Zappos doesn't sell paperweights though...
No, the advice would be killer. I don't even know what to order, and then when I got it I wouldn't know how to evaluate it to decide whether to return it!
Good point. Depending on brand and even individual shirt by the same brand, I can be a small, extra small, small slim fit, or medium slim fit... sigh

Short of inputting your detailed measurements, I wonder how a site can solve that.

There's a startup that does 3D scans of shoes and allows users to determine the perfect fit by asking about shoes they already own (can't remember the name). IIRC, they plan on doing clothes, too. That would be the ideal.

I once tried comparing official clothing measurements from various vendors online and came to the conclusion that they were all lying. Short of 3D scanning or painstaking measurement by hand, there isn't an easy solution. It certainly seems like a problem ripe for the picking.

>There's a startup that does 3D scans of shoes and allows users to determine the perfect fit by asking about shoes they already own (can't remember the name). IIRC, they plan on doing clothes, too. That would be the ideal.

Wow, someone please come forward with the name of this startup. I need new shoes, and if this works I'm spreading the news to everyone I know.

http://shoefitr.com/

They're just at demo stage at the moment. They eventually want to integrate this into your outlet's website.

Thanks for the link. I tried it a couple of times for a couple of different fits and I wish they had more refinement options .. like options to tell what fits to avoid and more than 1 recommendation, stability/pronation et al. for running shoes, etc.

Also sucks that for all my fits, it always showed an Asics product, a brand which I personally don't like as their fits / soles are the worst for me.

Hey, I'm one of the Shoefitr co-founders. The demo on the homepage assumes you're buying the Asics GT-2150 and just need to know what size to buy (and how it will feel). You can try it for all sorts of running shoes at http://www.runningwarehouse.com. Suggesting new products based on what you currently wear will be rolling out soon...
I know those guys. I think they're doing pretty well (have a number of decent sized deals, etc)

http;//shoefitr.com/

> There's a startup that does 3D scans of shoes and allows users to determine the perfect fit by asking about shoes they already own (can't remember the name). IIRC, they plan on doing clothes, too. That would be the ideal.

It would be really cool to hack a Kinect (or more likely, several Kinects) into doing something like that for clothing.

A friend of mine does custom dress shirts (http://propercloth.com/) and one of his solutions (besides the detailed measurements option) was to get base measurements from a whole range of retail shirts and let people pick a shirt that they already owned that fits them well and tweak from there (too long/short, tight in the chest, etc.) and then have a very liberal return policy (at least on the first shirt). It's definitely labor intensive to get started (both building up the measurements database plus learning how to tweak them based on the comments), but it seems to work well.
Very cool site! I'd love to see a few more "out-there" patterns.
Another application for Kinect? Not that I think its the same thing but might be an interesting experiment.
Online clothes shopping works when you want to buy something that you already know, know how it fits and maybe want an extra color or style. I usually shop for pants online, from brands that I know will have a good fit and cuts that I already have at home.
It is a hurtle when shopping in stores too. It would be nice if there was a fit feedback for each piece of clothing bought. Then the service would only show clothes that fit like earlier clothes that I have bought and rated high.
Displaying accurate measurements is not that hard?
Interesting idea. Went to http://dress.me and saw a "Your site is ready, please replace this index file" message and was immediately let down. Thought this was a release announcement.
Hey! Thanks for the feedback. Sorry for the letdown. My post about dress.me was for the AppSumo Lean Startup Challenge. I'm working on the landing page as fast as I can! Hope you'll stay tuned.
Are you US based? Please try to include filters for shops that ship to europe... i'd love using your service since i'd rather wrestle an alligator than go clothes shopping.
My advice: forget about making a great landing page--you need a simple page up now, as in today. This is getting buzz. Right now you should go to weebly and set up a splash page for dress.me that just has a simple email capture form for people who want to be notified of your launch. Find a friend or pay someone hundreds of dollars to do this today if you don't know how. If I don't get an email announcing launch, you can bet I won't remember about your service.

Good luck, and it sounds like a great idea if you can make it work!

I already use a service like this: my wife. Sometimes she brings clothes home, I try them on and she returns what I don't like. When I do feel like shopping, she makes it a very fast by bringing clothes in quantity back to the changing room. For going shopping my reward is that we always go to a Thai or Chinese restaurant for lunch afterwards.

I do go shopping voluntarily when we need to buy a nice dress for my wife before going on a cruise vacation, etc. She likes to get something that I like.

Way back when I was single, I bought some clothes pushed on me by sales clerks that later friends mentioned didn't look so great on me. For single men, I would advise waiting until you have a girlfriend with good taste - then stock up using her advice.

Dress.me might work, but it seems like it would be difficult to do using only questions on a web site.

>I would advise waiting until you have a girlfriend with good taste - then stock up using her advice.

Maybe don't mention this plan on the first date though.

Haha, I was in this exact situation once and it worked out awesomely. "I hate my clothes and I could really use your help" can be great first date conversation.

Besides, it shows that you're clued in. She will definitely recognize that you need new clothes before you do.

I would advise waiting until you have a girlfriend with good taste...

How would you know she has good taste?

My fiance bought a new outfit right before our first date, and he couldn't resist telling me it was new and asking if I liked it in the middle of the date. I did like it, so he had the taste, just not the inclination in general.

I don't think he got a single new article of clothing until we got engaged, when I started buying his clothes.

A great under-explored market. Hurdle would be there needs to be some sort of feedback loop of how the piece actually fits ON the customer IRL.

- Every body type is different and every label has different sizes/cuts.

- how the outfit fits makes up 90% of an outfit looking great

- target market lacks the ability to judge fit for themselves

BTW, I'm not a fashion expert but I married one.

tldr: sartorially skillz are important

I know "guys who hate to shop" is the target mass-market, but maybe the beta can be pitched towards the niche of guys who either love shopping or at least love evoking a personal sense of style.

As one of the later, I have to say that actual shopping is a pain and if I didn't live in a little town replete with boutique attendants I probably wouldn't shop.

I would like to second the "evoking a personal sense of style".
In complete seriousness, if the author is on this site... were you by any chance sitting in the table next to me at Cambridge Brewing Company a few days ago :) I was literally just talking about working on something like this with my girlfriend after a long terrible day of trying to buy a shirt ;)

I always find it fascinating how sometimes ideas can go a long time untouched, but when someone finally decides to work on it, it seems like 20 other people had the same idea at once.

This idea is genius! I really need this!
What are the "this or that" questions? As Jkkramer pointed out, fit is the most important thing. I want to input my body measurements, and have you spit out the companies whose clothes closest match my body measurements. For example, APC makes great jeans, but they're too tight for me in the thighs, despite being appropriately sized in the waist, knee and cuff.
I think the premise that men hate to shop is quite false. Men perceivably hate to shop because many men don't appreciate the art of looking beautiful and it's usually because our society doesn't instill that in men - we are instilled with this sense that women are fashionable and men don't have any fashion sense (which is bs). I actually really like to shop for clothes that make me look good but it has taken me a while to realize it and to realize that my style wasn't "unfashionable" it just needed some "guidance".

And that, IMHO, is what you should be targeting - not the fact that men hate to shop but that most don't have the confidence to refine their own personal style...

Geeks/men aren't slobs and we don't always hate to shop.

I hate to shop. And I'm a man.

Just to add more context so this doesn't come across as quite so snarky: I'm only validating the OP's concept that men hate to shop and offering that as a counterpoint to Ixiaus's suggestion that "the premise that men hate to shop is quite false." I'm a man. I hate to shop. I know many others who do, and many who don't. The OP addressed that in his post quite well.

In fact, I actually like looking good. I'm not a slob and I don't generally dress like one. The problem is that shopping is annoying. I don't have much fashion sense, I can't stand trying to pick a nice shirt out of hundreds of options with a half dozen variables each, and I never am able to tell what actually would look good on me.

A tool that did all the math and picking for me would be great. It's almost like a replacement for a spouse or mom that does the shopping for me.

Exactly. The goal of dress.me is to be a replacement for a spouse/mom/metro friend who is always available to help you with your purchases. Since I'm a woman, I understand this whole process pretty well. It's how I came up with dress.me--I was sick of helping out my significant other and guy friends when it came time to shop. With dress.me, they'll have the service they need whenever they want.
You do not hate to shop. You hate the fact that you do not know how to decide what to pick.
Right, not all men hate to shop. I actually mentioned that in my post. But for the guys who hate to shop (of which there are many), there's dress.me.
I think that, regardless of the premise being true or not, there certainly seems to be a potential market for streamlining what's fashionable for men's fashion.
"hate to shop" doesn't mean "slob". As a hacker (not going to speak for males here, and this applies to many female hackers too), I (and many other hackers I know) take an analytical and deconstructing attitude towards clothes: I care about comfort, and I care about meeting whatever expectation the people I care about making a good impression on want. Nothing else.

Ideally, I would like all people in the latter category to stop caring about choices of clothing as a factor, but that won't happen any time soon, and meanwhile I choose to put up with the way the world works by acting accordingly to get the result I want. Ideally, I want to spend a minimal amount of effort achieving both of those goals, so I can spend time hacking on something useful.

So, I'd welcome anything which helps me put less thought into the the myriad incompatible standards for "fit" and other factors that determine comfort, and less thought into the myriad unwritten rules that form the collective expectations of shallow people ("fashion").

I was an unfashionable geek for quite some time - I picked up salsa dancing it changed my entire perspective on outward appearance. I really grew to appreciate it, to appreciate the time people (and obviously women) put into grooming and dressing themselves in a manner that was unique to their own style but also attractive; an extension to that is enjoying the time it takes to find, select, and try on clothing for that purpose.

It's like going to Fry's and shopping for components to build a new computer - why do you think most contemporary non-geeks say, often, that they "hate shopping for computer parts"?

I would like all people in the latter category to stop caring about choices of clothing as a factor

I'm surprised you would say that - you may begin to notice that humans aren't computers with predictable API's to interact with. Inter-human communication and interactions are largely driven by sexual (perceivable or not) and biological queues. Smart and attractive (if you can dress well and take care of your body, you will be attractive) is an extremely powerful combination because the ultimate fate of humanity rests in the hands of our intelligence and a lot of the world will acknowledge you for your intelligence but if you want to make a serious difference - putting yourself together in a way that many non-geeks can relate with is crucially important.

Oh and clothing was never actually made to fit your particular body style - it's meant to be generic, you gotta get that stuff tailored! It's like custom fitting a computer for your needs, you have to do the same thing with your clothes, your body.

I once had the outlook you do, why do people like "clean" and attractive people so much? Why don't they see my intelligence more? On and on and on...

A large part of it is that in geek circles (or male circles in general) it's fashionable to say that you don't like to shop. I didn't like it until I tried to enjoy it. It's not the best but it's fun once in a while.
It's that way for chick-geeks too. I get hit on a lot by women in the tech scene and they can never figure out why I ignore their sexual and IOI signals in favor of women that are a bit boppier, wear heels and g-strings most of the time, and are on the extreme side of femininity.

Do I like intelligence? Greatly so, I get along really well with many women who are lawyers, doctors, &c... because those professions seem to attract really smart people that also like to be attractive when they go out casually. This is not typically the case for women and men in technology - it's actually refreshing to meet someone that is both a brilliant programmer/mathematician/engineer and cares about their outward presentation.

I'm not a slob, but I hate to shop. I tend towards a small number of brands specifically because I know if I buy them I'll be viewed as reasonably fashionable, and I know they're consistent enough that I don't need to try them on.

It'd be great to have more options, but I really don't want to spend four hours trying on clothes in a mall to come up with alternatives.

Man, you know you're on to a startup idea when your pre-implementation post about that idea can make the front-page.
Wont work out :)

This or that questions wont help. You might ask: blue or white? I say depends; you might ask: smart or casual? I say depends.

There are no questions that can 'solve' my style preferences and even if they do, the items I buy will not always follow them (maybe found some really cool green shoes that go with my blue shirt, which I wouldn't have bought if I didn't already have the shirt). I like moccasins for summer and oxford shoes for winter, seasons vary.

Even if you can somehow compile a perfect profile, then how the hell are you going to find items that match it? Very few retailers list things such as colour, season and material separately in a manner they can be easily gathered.

I sincerely suggest you to look elsewhere.

I REALLY like the idea but it's going to require a REALLY elegant implementation to streamline this.

I'm assuming you're going to monetize by eventually becoming a reseller or acting as an associate of sites you link to (could be wrong). If not, then I would advise this route over charging outright for using your service, as I'd be far more likely to use it that way.

All that being said, I really look forward to your launch so I can try this out. I am exactly your target audience.

Agreed. Monetizing dress.me as a preferred associate of clothing sites, or as a walled garden market where only you can offer select deals, would be far more palatable. I am also in your target demographic, but all I want is an algorithm that tells me when polka dots and stripes don't match.
Have you talked to any personal shoppers to see how your thoughts on how men want to be shopped for match up with their experiences?

Most of my more successful hacker friends in the finance industry whose wives are not interested in shopping for them went this route, and rely completely on their personal shoppers. Even the ones I would consider only slightly better dressed than random selection love the service.

Clothes shopping has remained one of those areas dominated by brick-and-mortar stores. I see three reasons for this:

1. Looking at photos is not the same as looking at the real thing;

2. Clothes are more than just the look. How they feel is also important;

3. You obviously can't try clothes on online. You can (and really need to) in a store. I have clothes that fit ranging from M to XL depending on the brand and style.

So there are those barriers to overcome. There are additional issues.

First, I read the dress.me blurb and it says that when you signup it asks you several "this or that" questions. A theoretically reasonable approach but one doomed to failure.

The reason is that people (men in particular) don't know what suits them. When someone says they like something, it means they're accustomed to it. This is a key point service providers like this need to understand.

It's why you see people seemingly trapped 10, 20, 30+ years ago with their haircuts, shoes and clothes. Typically this is how they looked and what they wore when they were teenagers and in their 20s. That sort of thing sticks because it's what they knew growing up (much like musical tastes tend to be) or even it's just the nostalgic angle: that style takes them back to probably what were more easygoing days.

Second, there are an awful lot of men--we geeks are particularly guilty of this--who have a completely utilitarian view to pretty much everything, including clothes. There's a reason the programmer stereotype is t-shirts and jeans. These clothes are comfortable, require very little maintenance, are cheap and require very little thought.

Clothes, like many things, are a statement about who you are as a person. Pretty much everything we do is some form of expression of who we are. This is even true of things like programming language choice.

So the problem we geeks have in particular is that we don't generally care about what kind of statement our clothes make, which in and of itself is a statement.

Anyway, watch any of the makeover shows that are on TV. Whether they be for men or women you will see the first thing the self-appointed style gurus will do is beat them out of their old habits into things that actually suit them. Asking them what they like would get you nowhere.

This is also why the cliche exists of women shopping for men. I think women are probably more naturally inclined to the "group" aspect of pretty much all forms of self-expression, clothes being just one. Just watch a woman--particularly a young woman--get dressed for anything and you'll quickly realize it's a group not a solo activity deciding what to wear.

Sites like this I think are seductive to those who start them, much like dating sites are. It seems like it should be easy, right? I think the reality has proven and will continue to prove otherwise, at least until these fundamental problems are somehow addressed.

The true meaning of "I hate shopping" is more likely to be "I hate making decisions about things I don't know about, care about or both." The "knowing" part can probably be fixed. The "caring" part is a much bigger problem.

"Looking at photos is not the same as looking at the real thing;"

You'd say the same thing about jewelry (BlueNile.com: 58M quarterly revenue) and shoes (Zappos.com: bought by Amazon for ~$1B).

(note: I edited this to say "jewelry" instead of "diamonds")- I agree loose diamonds are a commodity. An wedding ring you're going to wear the rest of your life is something I'd imagine people would want to see/wear before buying)

I don't think that's the barrier for clothes.

I don't think you'd say the same thing about diamonds: you pick the shape, size, clarity and colour. What else is there? If I were in the market for diamonds or diamond jewelry I see no problem with buying it online.

Shoes are a closer analogy. I would be very interested in seeing an answer to this question to those who buy/bought from Zappos:

When you buy shoes from Zappos, are you buying a style or shoe that you've previously tried on or bought?

Also, I think women's shoes are a different market to men's shoes. Women I think almost take it for granted that shoes, particularly dress/fashionable shoes, will be uncomfortable.

Again I take a utilitarian view to shoes. I have a hard time finding a pair that fits nicely. I'll buy lightweight runners/sneakers/joggers (depending on your lexicon) and then wear them virtually every day until they fall apart and I buy a new pair.

I imagine I am not alone in this.

Zappo's has free shipping in both directions, thus making potential fit issues far less problematic.

I've bought about a dozen pairs of shoes from them, and returned about six.

What if you could order the shoes and then return them no hassle if you didn't like them? That's what Zappos has done and it's lowered the barrier to buying something like shoes online.

Online clothing stores need an innovation like this.

'returning stuff' is still often a hassle, even with 'no hassle' policies.
Gap here in the UK lets you put your online order back in the bag, and stick it in the post with a checkbox question of why you're returning it. If all online clothes shopping worked like this I'd switch.
Here in the UK, ASOS (http://asos.com) have an amazing returns policy.

My girlfriend (and me to a certain extent) generally returns around 50% of her ASOS purchases after trying them on at home. You can return them in the same bag, have them picked up or drop them to any Collect Plus (http://www.collectplus.co.uk) location.

I buy shoes and clothing from Zappos all the time, because of their very lenient return policies. If I'm not sure what size or style to get, I'll just buy a few different combinations, try them on in the privacy of my apartment, and then return the ones that I don't like or that don't fit. It's a great system, and Zappos seems to even encourage this behavior.
You raise good points.

In particular, it cannot be overstated how important a good return policy is. It's also bizarre how many companies get it wrong.

Example: I bought some stuff from Bed, Bath and Beyond a month or two ago. I realized I'd gotten the wrong thing. By this time I'd misplaced the receipt. I was expecting a hassle when I went back to the store. I walk up to the service counter and ask what the return policy is. The women behind the counter says they have a no hassle return policy.

She said she could give me store credit no problem or, if I preferred, she could look up the receipt on the system with my credit card. If she could find it, she'd give me a refund instead. She did in fact find it. I didn't have to produce any annoying pieces of paper nor justify why I was returning the item.

After that incident I went and spent another $150 in comfort knowing that if what I bought didn't work out I could return it.

So my advice for anyone dealing with physical goods: make it as easy as possible to return goods and customers will spend more. Make them love your store/website/whatever.

I buy shoes from zappos. And yes, I only buy brands that I know are going to fit me well. Initially, I bought my first pair of sneakers because there was 1 year money back guarantee with total reimbursement (including delivery from and to zappos).

The delivery is fast. The prices are ok. So far I have never returned my shoes. They all fit perfectly and customer service is great!

If your shoes don't fit, or don't last, you aren't buying enough quality. Men's shoes are a solved problem.

But you need an expert, I don't think this is solvable on line.

Diamonds have a standard set of metrics which are verified for certification. They are essentially a commodity. I wonder what BlueNile's revenue for loose diamonds is vs. revenue for bands.

Shoes are slightly different than clothes. While fits do vary slightly, it's not even remotely close to the variations in clothing. Online shoe shopping also produces better results than clothing. Things like feel aren't are varied either and the details are not nearly as important. I wouldn't buy expensive shoes online, but for most types of shoes, I much prefer online vs. b&m. Partially because of variety and partly because of my size (13 US).

Contrast this to my online clothes shopping habits, where probably at least 50% of my purchases are returned.

Based just on my experience I would say Zappos does have the same problem, but I guess the margins are high enough to overcome it. I frequently buy shoes from Zappos and end up buying either a bunch of different shoes and returning most of them, or buying two or three sizes in one shoe and returning the ones that don't fit. So I think the OP comments were spot on. Just because something is a significant problem, doesn't mean it's something that can't be overcome.
Part of the reason BlueNile (and JamesAllen.com) are successful is that they can offer diamonds at much lower prices than any retail store due to the way the market is structured [1]. They buy directly from diamond sightholders, so they have larger inventory and lower overhead. Diamonds may be a commodity, but these retailers have a systematic advantage within that market. Typical retail stores charge a 100% markup over the wholesale cost; BlueNile's is about 18%.

[1] http://www.truthaboutdiamonds.com/truth-about/james-allen-bl...

"Have You Ever Tried to Sell a Diamond?" is also interesting reading. http://www.theatlantic.com/magazine/print/1982/02/have-you-e...

There's a reason the programmer stereotype is t-shirts and jeans. These clothes are comfortable, require very little maintenance, are cheap and require very little thought.

And they are simply always stylish, fit perfectly and you can hardly go wrong in them. Right? RIGHT???

Until you're going out on a first date at a nice restaurant, you're running late, and you discover that your shirt with buttons is in the dirty clothes.
Thats the advantage of geek clothing - you own several of each item based on how often you wear them, how many times you wear them without washing.

Hence:

1 suit

3 proper shirts

3 pairs of jeans

10 black t-shirts

Cletus,

Thanks for the rad feedback. I appreciate it. It'll make my product a lot better.

You're right, shopping online is different. But despite this, shopping online is a billion dollar industry that doesn't show any signs of being slowed down simply because it isn't taking place in person. I think if women (who, arguably, are more obsessed with fit/feel/etc. than guys) can shop online then there's definitely a way to make it work for men. That's what I plan on doing.

Also, great point about clothing serving as a symbol or a form of self-expression. I think you're spot-on about programmer types making the statement, "I don't really care about clothes," but a) it assumes everyone is making the same statement, which is problematic (we can't ALL have the same message to express since we have such a diversity of experiences in how we perceive the world) and b) it eliminates the possibility that a typical geeky dude never wants to look good, which I would argue isn't the case.

Nevertheless, great points and I appreciate them all.

as a geeky dude who does occasionally look good, when I started caring at all I found out what I should be wearing from a very analytical perspective. I first went to websites to find out what sort of colors, patterns, cuts of clothes I should wear based on my skin complexion, build, height, etc. Then I went to find what the current styles are and went to retail websites to find what the styles were that were currently being offered. Then I actually went to the store to try these things on to see how they fit and how well I wore them.

Buying something online really lacks any information on how the clothes will fit. There's basically that old saying and I don't see how it can be solved when buying online "wear the suit, don't let the suit wear you." If you could get the site set up to find locations near the user where these suggested clothes can be tried on/purchased then I think the site could be very useful.

As it is I was already interested enough to try to go to dress.me and sign up (only to find out it doesn't exist yet), however I wouldn't be willing to pay for it. If I could get a discount on the clothes the site suggested by being a paying member, then I may be willing to pay for it (but then it comes back to the conundrum I've already mentioned).

Vanity sizing doesn't help any, either. Sure, it might shrink a little in the wash, but some people are a little over-generous with that....
Hey Sonja, I really like the idea, and I've linked to it from multiple sources. I really hope your site takes off like I think it can.

I only have one piece of constructive feedback, which I hope you will pay some heed: Men have fragile egos. You should be wary of saying "Because guys hate shopping" or suggesting in any way that men do not have a sense of style. Yes, many (maybe even most) guys do not have any sense of style, or might hate the whole shopping experience. But I guarantee that using this sort of language as your tag-line (or 30-second elevator pitch) will turn away just as many guys from your site as it catches.

My suggestion is that you simply tout the benefits of this suggestion-based shopping. It's an obviously great idea, which I am backing 100%. Sell them on the benefits without making claims which will hurt their egos.

I realize that I'm an outlier, but to give you another perspective, I'm someone who shops online almost exclusively using communities like Superfuture.com and Stylezeitgeist.com to find new stuff. The site isn't for me but I'd still like to check it out just to see what surfaces for me once I answer the questions :D
Except a Levi's 550 - 36 32

Nothing to try, nothing to see, just buy and wear.

Oh, and Hanes tagless white t-shirts XL

Oh, and Nike slippers 10'

That's my basic outfit 24/7 and I can buy it all online.

Man, Zuck, you're finally filling out. Way to go, dude!
About the sizes: It's true that clothes range from M to XL depending of various factors; however, it is not something impossible to fix. For instance, it's possible to make an equivalence of "small of x1" = "large of x2".

Also, by asking the user to choose something he knows he's comfortable in, the website can get really interesting metrics to help determine the good size.

Finally, I guess it's always possible to give more detailed metrics of you (how much you weight, height, arms length, etc.). So, basically, it could be optional but if you're willing to spend a little time measuring it, it could be of a tremendous help. In fact, if I knew I could avoid big stores by taking a few measure of me, I'd do it right now.

That would certainly be helpful. Gilt.com does a thing where they tell you what size the model is wearing and then give you the models measurements. One step further that I would like to see is actual measurements of the clothing. For example I tend to need shirts that are fairly long in the torso. Sometimes tall sizes work, sometimes the standard sizes are fine. Since no length measurement is usually provided the only way for me to know is to try it on. Your never going to eliminate all returns, but I think there could be a big improvement by providing some measurements beyond what is typically available (waist, chest, neck, etc.).
We do give you the model's measurements but they don't necessarily mean much. The stylists for the models will pin the clothes to fit well so the pictures look good.

People who are models generally fall within a certain range of sizes, but it's still impossible to predict perfectly what will fit them, and you might not even have all the sizes available.

That's always annoyed me when walking through a store and seeing mannequins with clothes on that look like they are cut really nicely and aren't just made for a big fat guy. Then I walk around to the back of the mannequin and sure enough everything is pinned in place to make it look nice. I get that the clothes are made to fit onto the largest number of people, but it ends up like a design by committee type situation, where the end result is that no one really looks that good in the clothes. So yes, I can definitely see your point that the models measurements wouldn't mean much.

What I would like to see is specific measurements of the garment. The distance from the collar to the bottom of the shirt, the width at the bottom of the shirt, the width of the arms, etc. The few standard measurements that are usually provided with a dress shirt or a pair of pants are a good start, but they aren't nearly enough to judge fit. I've had shirts custom made (via the internet) that use the reverse of this process, where I provide them all sorts of different measurements and they make the garment to fit. They all fit very well, so I have hope that making this information available could help with the fit problem.

I agree that the site won't solve the problem it pretends to address if it's just going to ask you what you usually like and feed you similar stuff.

However, this can and should be bundled with a more assertive counseling activity: "we're not going to force anything down your throat; however, if you're not satisfied with the way you're perceived, and you think your clothing style is part of the problem, we might have some suggestion to offer".

Counselling should itself be structured in two levels:

* generic help for free ("If you have $PHYSICAL_FEATURE and want to be perceived as more $QUALITY, you should chose clothes which have $CRITERION. Beware that $CONTRAINDICATION". Could be raw text with a couple of diagrams, could be something more interactive)

* referral to one-to-one counselors, with a commission on their fee.

However, it sounds like a real problem, with real solutions to be provided, to people willing to pay for it (nobody expects to get clothes for free, no freemium competitor will undercut you), and with enough diversification possibilities to find one successful way to grow. As always, and especially for very personal services, flawless execution matters much more than the initial idea.

You're not far off the mark. I recently read that some $28 billion worth of merchandise is returned every year due to poor fit. Though I have no idea what percentage of the total expenditure that is, judging by the effect it has on the major driving forces of fashion (namely, none), it must be pretty small. About 4-5 years ago, a company in California did conduct some research into the sizing of women's clothing, and some of that has led to changes trickling into what's being offered on the shelf. But the research was conducted only on women, and the company doing the research even admitted that their population sample was insufficient. From what I can tell, all of the basic sloper patterns that ready to wear garments are built from get their standard sizing from... nowhere. Or a mysterious table of measurements dating back to the 1940s. Take your pick.

Compound this with the total lack of quality control in garment manufacture and you begin to see why shopping is such an ordeal. The same brand and fit (model?) of pants from Dockers, Levis or the Gap will fit you differently, depending on the color of the fabric. Typically, the darker the color of the garment, the more snug the fit. Sounds ridiculous, right? Lighter fabrics tend to relax out more. It's all about the fabric content. Raise your hand if you've ever washed something and had it either get smaller or bigger, or become completely misshapen. Quality control is done on the first hundred or so garments that come out of the factory. After that, it's a free-for-all.

People don't know what suits them because there is a very real learning curve to the whole process of getting yourself dressed. This is why most women shop and dress in groups. Institutional knowledge is hugely valuable. So is a cloth tape measure.

I watch What Not To Wear. They make it look easy. Then they make it look hard (the "victim" almost always cries). Because drama sells. But behind the scenes is an entire staff of people who follow fashion trends, understand a great deal about ready to wear garments and know where to go and what it costs. That's a full time job. Nobody has that kind of time, and it's a barrier to entry.

Not caring about what kind of statement our clothes make is a learned behavior. The fashion industry does not care about the happiness of the customer. If you don't believe me, find a girl who won't slap you for it and ask her about her bra. So if they don't care, why should we?

It might not always be 'poor fit'. My wife buys multiple items, keeps the one she wants, and has me return the others. A cashier inevitably checks 'wrong fit' on the 'reason' area of the return form, even though they probably fit just fine. They didn't 'fit' my wife's mood, perhaps, but certainly would've fit her body just fine.
So many people I know (my gf included) do this, both buying for themselves or for the men in their lives.
I've found myself doing this more frequently. Basic reasoning is that unless I'm at some store that is far outside my normal commuting path, I'd rather spend 20 minutes just grabbing things that look roughly right. Then I can try them on at my convenience and return what I don't like sometime over the next week or two.

This saves me time in the store and also makes the decision less agonizing since I can make it over a few days.

So, yeah, you're probably dead on about how 'wrong fit' can be interpreted.

Couldn't part of this be mitigated by having the user input their exact measurements? That's the first thing that happens when you visit a custom clothier. Having this input, it would be possible (not necessarily easy) to match this with the clothing. The harder problems to solve like this are the better ones to go after, b/c they are hard to replicate, and indicate a willingness to go the long mile to make the service more useful.
Unlikely. The problem is at the source. Sometimes the "size charts" are off by as much as 4" in the waist size, based on my observations.
Read this waist comparison recently. Apparently even the most accurate brands are not correct.

http://www.esquire.com/blogs/mens-fashion/pants-size-chart-0...

I've done similar things with women's clothing. Gap/Old Navy are by far one of the most 'generous' with the concept of ease, especially in what they consider to be plus sizes (anything over a 12, from what I can tell). Any good tailor will put an inch or so of ease into a garment. It is as the term implies, a bit of room to keep your garment from tearing when you move around. What's even more interesting is how women's sizes are scaled. Between the smaller sizes, the measurements go up half an inch to an inch. When you get to the larger sizes, where the waist is above 28", the delta between the sizes can be as much as four inches. To wit, if you are small, then you get more choice in how much ease you prefer. If you are larger, you get either too tight or too loose.

So it doesn't surprise me that there's "vanity sizing" in men's trousers. Not even a little bit. This, too, makes for a tough call when it comes to getting dressed. Camel toe or saggy butt? Hm.

(eta: sorry for devolving this discussion into a rant on ready to wear clothing)

A custom clothier has years of experience (and sometimes even a special school of though) what and how to measure.

IRL, you get people who miss their measurement unit (cm or inches seem to be complicated). Or they misunderstand instructions and thus just enter 10 cm while they should enter 10.5 cm.

However, there are online stores for custom made shirts (with lots of measurements) and it sometimes works, depending on the dedication on the user's side.

I've had good luck with online stores for custom shirts as long as I've had someone else assist with measurement and been careful to follow instructions. Generally it's best to stick with one of tailors who asks for a more detailed (but, not necessarily more complicated) set of measurements.

Also, try doing the first few shirts individually (typically there are discounts for buying 4-5 at a time). You may need to have 1-2 great-but-not-perfect shirts first. But once you nail the measurement, it's easy from there on out.

It doesn't work that way. You go buy clothes that are as close as possible to your fit, then you take it to a tailor and have that last inch brought in/up etc...

Believe this: tailors aren't just for fancy clothes and they aren't expensive. I take all of my jeans to my tailor and have them hemmed to the exact length of my legs because not a single clothing manufacturer makes clothing that fits my length!

Compound this with the total lack of quality control in garment manufacture and you begin to see why shopping is such an ordeal.

Anecdotal point, I bought a pair of black jeans from the Gap (4 months ago), having tried on several other colors of the same model (size/cut), each fitting different. Since I could not find an identical fitting pair in another color, I decided to get a second pair of black jeans (exact same).

Being paranoid, I decided to try on the second pair before purchasing, and it fit differently than the first.

I decided to try on the first pair again to make sure I was not going crazy. Exact same pants, exact same UPC, different fit.

If I can find a good piece of clothing that fits me well, I tend to purchase several of them at once (in the same exact color/style).

I use another startup called http://hendrickspark.com/ to solve most of those issues for myself.

You have a "style expert" who you meet with over Skype video. They send you a box of clothes to try on and review with your expert over Skype video. Any items you don't like or don't fit you put back in the box and send back. They include the return shipping label in the box so you just have to put the label on tape up the box and have FedEx pick it up. You only pay for the items you keep (no shipping charges or extra fees). They try to make the process as painless as possible.

Over time as you meet with your style expert, it's always the same person, and get to know each other they get a better sense for what you like and don't like as well as keeping track of things such as sizes and fits. They also recommend what things work well together so you know what things to wear together, etc. They have definitely pushed me out of my t-shirt and jeans comfort zone, without going to fashionista or anything.

The primary drawback is my clothes budget is definitely higher than it use to be, as most of the clothes are significantly more expensive (no $20 dollar jeans) as they tend to come from more boutique and small manufacturers.

While that probably sounds an awful lot like an advertisement I have no connection with Hendricks Park other than as a happy customer.

It seems like most of these services are mostly boutique clothes with higher price points. Is this due them just going after more affluent customers, or is it difficult to get wholesale prices from lower cost vendors?

Seems like others might be drawn to this if they didn't have to shell out $200 for a pair of jeans each time. I definitely get the desire for premiere clothing/shopping just wondering if it can scale down the price line and still work.

What's the advantage of this over going shopping with a fashion oriented friend?
Your fashion oriented friend may not be available and/or run out of patience, plus, you have to be shopping too, and you are limited in geographic area to where you can obtain clothing (constrained by time and travel time).
While this sounds interesting and made me check out their side, this _is_ on a different scale than the issue we're discussing here.

Two things that stand out and (deliberately) separate this site from the casual online shop experience:

"Hendricks Park is a _luxury clothing_ service for men who have better things to do with their time than shop for clothing."

"Men who enjoy and value our service the most, tend to buy at least $1,250 in clothing per season."

Dumb question, in fashion, are there four seasons per year?

Specifically, should a man using this service budget $5,000 a year for clothing?

Looks like two seasons a year, spring and fall.
Is there a women's version of this service?
I may be an outlier, but I do my clothes shopping online. Let me tell you how they have overcome the problems you have mentioned.

Most online clothes shops I've seen have a really good return policy and free postage. They encourage you to order more then you need, and as well different sizes. So you effectively get sent a whole bunch of stuff to try. You try it on, keep what you like and send the rest back for a refund. It's even better when you're ordering online from shops that have a physical presence as you can just take it back to the store and get a refund instantly.

Exactly this. The only reason I will buy from Bonobos is because if it doesn't fit(and they seemed to have changed some of their cuts recently so this has been happening a lot) I just send it back (free postage) for a full refund. The only waste here is time.
I buy online alot as well. In addition to liberal return policies, many retailers (ala blackbirdballard.com) will post individual measurements of each dimension of a piece. For jackets, you can measure one of your existing jackets or your body to see how it compares.
"Pretty much everything we do is some form of expression of who we are. This is even true of things like programming language choice."

The real question is whether there is a correlation between clothes and programming language choice. Do lisp users wear highly functional clothing that's really ugly to look at? :)

In the US it seems that most people are wearing clothing that's several sizes too big compared to in Europe, so it might work there because there isn't much of a difference between big and a bit bigger.
Perhaps these can be handled by approaching the problem similarly to the way Rent the Runway does. In the Mixergy interview with the founders (http://mixergy.com/hyman-fleiss-rent-the-runway-interview/), they discuss their realization that it's all about the experience. Of wearing something new. Of having it fit just right. And most importantly, the experience of the occasion they wear it to.

They were able to base their successful decisions on that assumption. Like using same-day shipping. Sending multiple clothes for the price of one to allow them to use the one that fits both them and the occasion. And more recently, including any accessories that can go with their choices.

I think some of these ideas can be generalized. As a shopping service, you can overcome all three barriers by sending multiple clothes based on the "this or that" questions. Or current trends. Or a both. This allows the buyer to make their final decisions within the comfort of their own homes. They can then send back all but the clothes they keep, if any.

I'm pretty certain men won't use this service for renting (though what do I know, I haven't tested this assumption), but treating it as such, you anticipate returns to be normal. The service can possibly learn what works for recurring customers (what fits, what general style they keep, etc), and lower the return rate. Furthermore, it can find trends in the "this or that" questions vs return rate to better predict as to what will be kept. It can even make fashion suggestions and educate on the subject via email/blog. I think us geeks would be more open to fashion advice if there were theory and stats to back it up (well, I would anyway; there's mountains of theory behind design, why not fashion?). Translate the emotional into the technical. Base suggestions on what both visually pleases the crowd and feels good to the indifferent individual.

Does this sound any more feasible?

I think, in general, that there are likely a bunch of unmet needs that are fairly obvious to women, and less so to men. Because of this, I think that women entrepreneurs have an advantage in seeing these earlier.

When you see a dominant hegemony (as in male-dominated technical startups), it's useful to imagine yourself as the minority and try to see what your hegemony is missing.

It's hard to put yourself outside your range of experience, but it's a useful exercise anyway.

Great idea, and well stated. I'll add a plus-one for filtering based on shipping territories.

It ties in with other peoples' comments regarding personal shoppers, but once you get past the initial mvp stage, I think there's an opening for adding the ability to ping my clothing-savvy (female) friends to say "what do you think of this?" There's possibly an exploitable network effect in there.