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It took me a couple years to get to the point where I could buy a plaid shirt, and I figured that as soon as I did it would stop being "cool".
That is not me in that video.

I wouldn't be caught dead in a store like that.

I'm definitely the one in the second video. Cool idea! I think a lot of people could use this service.
Funny. though I'm just scared to imagine what amount of nuclear flak would a 'symmetric' article take.

Just imagine the title "Girls love to shop, could this be you in the video?". so much for gender equality.

It is less about equity than it is about tired, damaging stereotyping.
I actually get allergic reactions to shopping malls. I'm not kidding; dry eyes, headache and joint pains slowly start to show up if I spend more than 30 minutes inside one.

Consequently, I tend shop for clothes almost as if it was a military maneuver. Deploy in shop, locate any pair of pants that fit predetermined criteria, pay, leave.

I used to hate shopping with my grandmother, mom, aunt, and sister. It usually meant an all-day outing going to nearly every aisle of every store and lugging around incredible heaps of stuff. Endless eye-glazing hours. Much of it spent not actually buying anything, but just looking at things. It seems like it should qualify as a form of torture.

I loved to go shopping with my grandfather. Whether it was clothes, electronics, or groceries. We knew the layout of the store. We knew what we were going to get. We went in on one side of the store and efficiently navigated the quickest round through it to hit the areas we needed without wasting time in those that we didn't. We went down aisle, things went into the cart, we hit the checkout, and out to the car and back home.

As an adult, I'm the same way. The only difference is that I have the benefit of technology to make it even more efficient. Where the women in the family would have spent an hour or two grocery shopping and my grandfather and I would have spent thirty minutes, I'm able to spend five minutes. Login, click a button for the same order as last time, and answer the door the next day when they delivery it into my kitchen.

I have happily not been inside a mall in over a decade or a grocery store for almost a decade. It seems like such a small thing, but liberating yourself of some of those chores is so damn wonderful! Now, if only there were an alternative for doctor visits, so I didn't have to waste an entire day of my precious time to spend five minutes with my doctor.

I couldn't care any less whether my plaid shirts are considered cool. I learned a long time ago that if you fall into the trap of letting girlfriends, wives or GQ Magazine tell you how to dress, you just end up with a closet full of clothes you're uncomfortable wearing. Be happy, be comfortable, wear what you want to.

"Dressing up is inevitably a substitute for good ideas." -PG

http://www.paulgraham.com/bubble.html

"Be happy, be comfortable, wear what you want to."

That's the key. I think it's better that a guy develops his own style than try to mimic another.

That being said, I don't think getting inspiration from magazines (GQ) or websites is a bad idea as long as you make the choice based the or your own rationale rather than blind agreement.

My wardrobe consists mostly of geeky T-shirts, from cons or the Internet. I hate shopping in malls. I'll be thrilled if this service works as advertised!
Wow, if men weren't the target here, there might be accusations that it's sexist.

Anyway, you know what? I don't like to shop. That's why I buy my groceries online and my local store delivers them the next day. I spend five minutes to do it and someone else goes to the store and brings it to my kitchen, so I can avoid the driving, the parking, the lines, the kids, the checkouts, the bringing the groceries in. Same for as many other things as I can buy online instead of in person. Including (as much as possible) clothes.

See, I'm a male. I don't particularly care if I'm wearing the latest fashion or if I've adopted the Bieber haircut. It doesn't matter to me. I buy clothing that doesn't have logos or advertise anything on it. I like black clothing. I also don't like to waste time with hairstyles. I shave my head and have for over a decade. It saves me time and looks fine. Just like pants or slacks and a black shirt looks fine. Because, again, I don't build my entire life and self-esteem around what I look like.

As long as I look like I showered and didn't sleep in a gutter overnight, I'm fine. And, believe it or not, I've never had a woman give a damn about my shoes or the label on my clothing or whether my hair was feathered. They always want to know what I do for a living and what kind of car I drive and whether I own my own home and what part of town I live in and what school I went to and (in roundabout ways of asking) how much money I make. None have ever given a god damn about my clothing. And if they have, I didn't know about it and didn't care. And still don't.

Now, who's going to write the follow-up article about how Women Shouldn't Shop, because they don't know what they're doing when they're buying a new stereo or computer or television or car or other (insert stereotype).

I order a lot from Amazon now, but there's no local store that will do that... I really don't mind waiting a day or 2 for the groceries if I can skip all that other nonsense and code or play games instead during that time.

Sadly, the last food I bought on Amazon was about 30% cheaper than the grocery store, too. It's practically forcing my hand at this point.

Depending on the size of your city, you may want to check around. In the places I've lived the past decade (Portland, San Francisco, Denver) stores have had online ordering and delivery for over a decade. Safeway, Kroger, and Albertsons and if places like Homeshop, Peapod, and Webvan are still around, they do a similar thing. I suspect those chains only deliver in cities large enough to justify the cost of infrastructure, though.
Being a "male" has nothing to do with your issues.

Maybe the girls who did approach you did so despite the fact that you're dressed and groomed like mental patient (I say that lovingly fellow HNer)

Anecdotal evidence is fun and all ("I have a GF so I must know everything about women!") but to think that wardrobe means nothing to the opposite sex is just crazy.

As soon as you enter the room your entire presence is scrutinized immediately by every woman (and most likely some men) in the room. Most won't need to even ask you how much you make after they approach you, they will have already deduced it from what you're wearing and your personal grooming (or lack thereof)

The gist of my point wasn't that women don't necessarily care about clothes and hairstyles and so on (of course they do) as much as it was that I don't care that they care. You can dress nice and look good without following whatever the latest fashion was dictated to society in this month's GQ and Vogue and unless you're really into primping, you may as well just go with a look that is relatively timeless.

Frankly, you have to determine that you're living your own life at some point and stop caring so much about what everyone else thinks to the point that it impacts the way you even clothe yourself (beyond stuff matching, belonging to this century, and being clean). If anyone here, for example, really cared that much, they'd all be race car drivers and pro athletes.

"Anecdotal evidence is fun and all ("I have a GF so I must know everything about women!") but to think that wardrobe means nothing to the opposite sex is just crazy."

Precisely. I think having a style does say a lot about a person. This doesn't mean having to dress in luxury brands, it means taking a stance. Women definitely notice a guy who takes the care for their appearance. That doesn't mean she'll instantly be attracted to him because obviously attraction relies on a combination of factors, but it does give him a slight leg up over other guys, not unlike personality, height, facial appearance, etc.

Caring about appearances isn't a bad thing. It's not like men don't judge women by comparable metrics.

I'm with you. But I do know guys who Do care. They aren't All gay, and some of them look very good.

In fact one fellow, Josh, never wore a single company clothing giveaway in the entire time I worked with him. We even got leather jackets after one release, and he gave it away! No logo, stylish, just not his style.

I don't think he spent any inordinate amount of time on it, he just had opinions.

Oh, I know there are guys who are into clothing and hair and all of that, just as much as there are guys who only wear one color of clothing (so everything always matches!) and usually take a trusted female along to make sure they don't do anything too stupid.

But that is a case where someone has chosen to care. If you have an interest in something, it's completely different than someone volunteering their opinion that you suck at it and need someone to do it the right way for you. Especially if it is of no interest to you or you're fine with your own choices, thank-you-very-much. What they're really saying is "let me help you, so that I'll stop judging you".

I also hate to shop. When I buy clothes, I'm in and out, like a ninja. And if I had my way, I'd wear my jeans / t-shirt / hoodie combo every day for the rest of my life.

However, there's times when your clothes matter and your usual garb won't cut it. Want good service at a posh restaurant? Doing a bizdev presentation at an ad agency or media company? Getting deposed in front of a grand jury? You'll want to have a broader sartorial range. It's not about your self-esteem, it's about the (often unfair) reactions of others to your looks.

I haven't seen the product, but a dress.me-like service could be useful here. In the past, I debated signing up for hendrickspark.com, an online personal shopping service, but I don't spend enough on clothes to get value out of it. Perhaps dress.me will be better suited for someone who only occasionally buys posh clothes.

That isn't me. I am male. I enjoy shopping for clothes and other items. Walking around a mall with friends is a good way to spend an afternoon. (And carry a set amount of cash instead of a credit card to prevent overspending)
I'm glad to have figured out at the age of 20 or so that dressing well (or at least reasonably) is a small investment of time and money that pays off hugely in the long run in terms of how other people treat you. If you're smart and poorly-dressed, you're that useful freakshow. If you're smart and well-dressed, you're the master of the freaking universe.

General principles:

a) Spend some damn money. I'm not gonna tell you how much, but if your spending on clothes is way below average for your age and income bracket then you probably look like a slob. If you earn $100K a year and your pants cost $15 then you have a problem.

b) No free t-shirts. In fact, no t-shirts with logos on them. In fact, no visible logos on any of your clothes at any time. Legible words are generally a no-no.

c) When in doubt, plain colours, nothing too garish.

d) Fit is everything.

e) When in doubt, read magnificentbastard.com

"If you earn $100K a year and your pants cost $15 then you have a problem"

Disagree. If you go to second-hand stores or flea markets, you can find great deals. And in fact, you constantly wear vintage, that's a specific style that speaks just as loud as wearing a luxury brand.

That said, you are right about fit. I think it's actually better to get cheaper stuff but spend the 'savings' on tailoring because that has much greater benefits than the brand.

If you're already making $100K a year you don't have a problem to begin with. If your lack of ability to make friends and influence people prevents you from making said money in the first place, then yes you may have a problem.
Alternately, if you have the talent and personality, nobody cares what you dress like. At worst, you're eccentric.

I have a hard time believing there is anyone out there in the world who doesn't have the basic common sense to dress themselves well enough to make it at a job interview, a date, or some formal or semi-casual event. Nobody really needs help figuring out the four pieces of clothing that are appropriate and look fine on them, do they? If the advice they're paying for is that basic and simple, then I'm going to start a service where for only $10, I tell you to throw away your stupid junior high school AXE and replace it with something like a nice Bvlgari.

Look at Henry Rollins. Smart guy. A bit eccentric. Looks fine. Does it take a rocket scientist or a hired-hand to tell you that a nice pair of pants and a plain black tee shirt is a good look? Or that untied Converse and sweatpants isn't the way to score points with people who don't know you, yet?

Also, there's a world of difference between "let me dress you like you're my Ken doll, because you have to be hip to the latest fashions in this quarter's fashion magazine" and "hey, don't dress yourself like one of the Kids of Whidney High".

"Guys, are you emotionally immature man-children who have long been considered 'adults' but still need mommy to help you purchase clothing? Don't boldly take on the responsibilities of adulthood, as your fathers did; celebrate your immaturity!"

I don't have a problem with anyone shopping by 'net, I'm a guy and yes, I do somewhat hate clothes shopping. However, I strongly object to the infantilization of the ostensibly adult men in these videos. There is a trend in our society towards perpetual boyhood and I think it's damaging to the male psyche. Just as women are told they're ugly and inadequate in order to sell them things, men are told they should never grow up or stop indulging themselves in childish ways (to the same end).

I like the business idea but please don't encourage and promote the man-boy image as laudable. Good, short article on the subject: http://www.inthesetimes.com/article/2526/

(for identity politicians: I am a 26yo man with 2 kids, I very much fit the "perpetual boyhood" template before I became a parent, and initially accepted my adult responsibilities only reluctantly. I'm not just speaking down here: this article describes me as well.)