Ask HN: How do I dress better?

64 points by randomJoe69 ↗ HN
I have been a hoodie and jeans kind of guy for a long time.

But now that I graduated and started working as a developer, I feel that my attire might be getting in the way of being taken seriously.

Do you have advice (or service) that would help me up "my game" without seeming that I try too hard?

64 comments

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Unless you want to put a lot of effort into this then just buy clothes with the best quality fabric you can find (you can tell quality fabric just by feel).

Not only will your clothes feel great, as a side effect you will be stylish without being fashionable. Quality never goes out of style.

Edit. I should add that top quality fabric is never wasted on "fast fashion" so the clothes will always be a bit more conservative and so will remain stylish for longer.

This is one area where men have a massive advantage over women. As a man you can buy well made clothes with quality fabric for less than women pay for wear-once garbage.

How do you define best quality fabric?
Feel. Really all you have to do is go around and feel the fabric from a range of stores (from cheap to outrageously expensive) and you will quickly learn to be able to tell good from bad fabric. Once you know this go back through the stores and find the high- to mid-priced clothes with high quality fabric.

Edit. A lot of designers will make a limited number of items with fabric that is much better than the pricing point would suggest. My guess is they have dreams of being in Paris or Milan and so sneak in more quality than the collection calls for on a few items - the "yes most of my designs are compromised by commercial concerns, but look at this one shirt" effect.

Gotcha, but I believe from personal experience that there are tons of fabric blends that are cheap yet feel fantastic, how not to get tricked?
Well with experience you can tell the difference, but you can always look at the label if in doubt.
If you have any friends who routinely dress well, ask them to take you shopping. In my experience, they really enjoy it (that's why they dress well themselves), and would appreciate the challenge of helping you to look and feel your best.

Another approach is to go to a store that sells the kinds of attire you'd generally be comfortable in (i.e., the kind of store that sells attire for people like you, and ask a shop attendant to dress you. Obviously there's a risk there that they'll just try and sell you overpriced stuff that doesn't suit you, so you have to be confident enough in your own judgement about what you'll feel good in, and be assertive enough to not let yourself spend more than you're comfortable with.

You could also just try browsing fashion sites online to find outfits that you like. But don't feel like you need to get fancy and complicated (and expensive). Just go for simple outfits made of good fabric and that fit your body shape well.

This worked like a charm for a friend of mine in college: Go to a clothing store and buy exact sets of clothing off of the mannequins that you see.

He knew literally nothing about fashion, but was consistently complimented on his clothing.

This is a surprisingly good approach especially at stores where the person dressing the mannequins has some sort of clue.

The only downside is you will often end up with sets of clothes that can't be mixed and matched well.

Another downside is that you will mostly buy the most expensive clothes in the shop.

Yet another one is that you will often buy clothes very specific to that year's collection and will look outdated soon.

Mannequins rarely are with the cheaper and/or classic clothes.

Yes this is true, but neither of these are a huge problem if you just want to look fashionable and have the money.

My actual advice is buy the clothes with the best quality fabric.

Never understood how clothing can get in the way of confidence. If you know your stuff, then being taken seriously should not be a problem. Remember, with this question, what you're really saying is, "How can I best mask myself so that others accept me based on their own insecurities?"... Blah! Good luck.
Man or woman, I'd ask a female friend for help. In my experience women have much better eyes for dress than men, for either men or women actually. See if you can't convince someone to come along shopping with you, the second opinion is very valuable.
Looking at most husbands I would disagree with this statement :p
One of the usual complaints women have about their husbands is that men don't take their fashion advice into account. Sometimes this gets to the level of women dragging their husbands into clothing stores to buy new clothes that are presentable.
My brother did this. My first question when I saw him: "are you dating?". He took the wife of his best friend one afternoon shopping and in one or two stores they were done.

He does this once every year now. The difference is amazing. Caveat: she actually looks better dressed than most women.

My sister used to play that role for me. She took me to the store twice a year and that was it. I often got compliments for stuff I didn't like myself but she had insisted on.
Just replacing your hoodie with a tahirt would do a lot. The next steps are replace sneakers with more adult shoes (Eccos for example, or another brown shoe) and replace the t-shirts with button shirts and undershirts.

Honestly though I'm 40 and I wear jeans and a t-shirt. I've been working as a developer for 20 years. When I started the jeans and a t-shirt thing was not accepted like it is now.

It sounds like you don't have a particular style in mind, so based on that assumption:

(1) If you go to a nice department store like Nordstrom, I believe you can still make an appointment with a personal shopper. That might be the best way for you to try new styles while also getting to feel the fabric in advance and get clothes that fit you well.

(2) If there are people you think dress nicely in a way you'd like to emulate, compliment them! They'll appreciate it. They might tell you where they got the outfit. And if not, you can ask.

(3) If you go to a clothing company's website like JCrew.com, they'll have a lot of pictures of people wearing full, stylish outfits, that might start to give you ideas about how to put your own outfits together. On JCrew I believe they even have a page called "What to wear" with links to all the items in each picture.

Good luck out there!

Much the same as any creative activity, thoughtful study and deliberate practice will take you a long way.

- Look at what people wear when you walk around the street. Who dresses well? What do you like about their style?

- Try on lots of different clothes, including stuff that you wouldn't normally wear. What works? What doesn't? Why?

- Get a full length mirror. Look at yourself before you leave the house everyday. Take some time to try on outfits, how can you combine clothes you already have into new outfits.

- Most important -> Have fun, and dress for your taste not what you think others want to see.

It really depends on your office environment. In most companies in the bay, a hoodie and jeans are completely fine and it will likely be distracting if you dress 'too nice'.

Take cues from how most people dress in the office and target that level of formality. If most people are t-shirt and jeans, just stick with what you're comfortable in. If most are jeans and a button-up shirt, do that.

Yeah, it's conformity, but if you're concerned your attire is affecting your perception, the easiest way to fix it is to match everyone else.

I work in the south of France and not in the bay. Here everyone looks like they work part-time model.
Girls have always said to me that the key thing is to get clothes that fit properly - this means asking help from fitters at the clothes shops and trying on LOTS of stuff till it looks and feels right. Take alot friends who are girls who are interested in fashion.

Find "your colors" - i.e. general color directions that look good on you. Ask people (typically women because they tend to be interested in such topics) what colors they think would suit you.

I made a decision a long while back to never wear tshirts again. After a certain age they look sloppy, not cool. I always wear a collared shirt. Equally I never wear short sleeved shirts - I roll up the sleeves of long sleeved shirts on hot days.

Get some nice brown leather shoes and some nice black leather shoes.

If you live in a cold climate buy several smart jackets including some leather jackets.

Other people here have suggest flicking through mens fashion magazines like GQ for ideas.

Start noticing what smart looking men are wearing.

Get several high quality white collared shirts and several high quality black collared shirts, these will go with a nice pair of slacks.

Buy a suit and not a cheap one - get it properly fitted and try on at least six suits before you buy one - wear it without a tie when you are going out with one of the white or black shorts mentioned above.

Accessorize - get a nice watch and belt.

Keep your hair regularly cut.

Don't buy cheap clothes - this is important. Having said that, do buy quality clothes that are on sale, or find factory outlets that sell the high quality brands at lower cost.

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Or, if all of that sounds overwhelming or a huge time sink, hire a style adviser. Alternatively, let a stylish friend help you out.

If you do want to take the plunge, reddit.com/r/malefasionadvice is one of the best organized and most complete resources out there

couldn't agree more.

for suits though I'd suggest skip off the rack and do made to measure, or if budget allows, fully bespoke.

another thing, almost never wear your jacket "naked", get a pocket square. White linen / cotton in a presidential fold for formal occasions and bright / patterned silk in a casual puff to hit the town.

WRT short sleeved shirts: The Apollo-era NASA engineers pretty much all wore short-sleeved white shirts, black slacks, and a black tie. The image has stuck in many people's heads as what a professional engineer should look like, even younger people who've seen movies about the era like Apollo 13. It's also still a popular style at NASA for looking professional (photo ops and such).

Of course the reasoning for short sleeves is that graphite dust would stain long sleeves. Likewise for a black tie. Since drafting using pencils is pretty much nonexistent these days the need for the style is gone. Now it's just used to project an image of competent professional engineering.

It's also much more common among engineers in disciplines where they could get a PE than among programmers. Code monkeys don't match, sparkies and gearheads do.

Emulate the style of someone on your work environment you consider is taken seriously and with a style that you personally like.

Fashion changes a lot from one group of people to another. That's why it is important to emulate someone from the same group.

Emulate is important, as you don't want to copy and look exactly the same.

That you like is important, because it shows when you are not comfortable on some clothes. Wearing something you don't personally like would be "trying too hard".

I wouldn't worry too much about not being taken seriously in a hoodie and jeans as a software developer unless you're working at an extremely traditional company that doesn't have much of a focus on the dev org. Hoodie and jeans is pretty much standard.

If you'd still like to dress "better" in general, the /r/malefashionadvice subreddit has some solid resources on the sidebar that you should check out.

It was the same for me when I started my internship and now transitioned to full time. I found [Ashley Weston](https://ashleyweston.com/), who is according to herself a celebrity mens' wear stylist. She has a good set of essentials which I basically all bought (except for the suits due to monetary reasons) and I think this has really helped me.

I am not affiliated with her or whatever, just follow her advice myself and enjoy her content.

Here's what have been working well for me. I wear dress pants (not jeans, not chino - Izod for example), colorful shirts (Nautica are my favorite) - always tucked in, good looking but comfortable shoes (not sneakers). I make sure they are always reasonably ironed. And silly socks - Happy Socks are the best. During the summer I use short sleeves, long sleeves in the winter if I feel like. I never use a tie, but you may if you feel like.
I would recommend keeping your current style if you don't want to try to hard, and simply tweaking it with new items.

For example -- keep wearing jeans, but buy a couple pairs of nice, dark/black well-cut jeans.

Instead of wearing a sweatshirt hoodie, wear a nice pullover sweater (H&M sells a nice waffle-texture sweater for fairly cheap, I got mine on clearance for $5 and I've worn it for years now).

Button-ups can easily look too formal, but flannel is a good middle ground.

Some nice-fabric solid-tone tshirts are a good basic, as well.

Now that you have a few pieces, you can mix-and-match as well. Sweater + flannel underneath, unbuttoned flannel with tshirt underneath, etc.

For shoes, instead of wearing cheap running shoes, find some nicer-looking neutral-color sneakers (might be worth looking thru https://www.reddit.com/r/Sneakers/comments/2e9b1o/we_should_..., but I can't vouch too hard for it). Depending on your style, you might also want some boots -- I have some big black Doc-esque boots that I love, but brown is a less-punk choice that's a classic.

FWIW: I'm not a guy, but this advice is pretty gender-neutral.

Good luck!

Same thing, I'm a TShirt + Jeans type person and didn't understand this at first.

Make sure the jeans you have don't have holes / rips in them. Get some new TShirts - don't wear older / faded ones.

Make sure what you wear is in good condition, and you should be good.

If you're not happy in boring shirts, then there are some that have prints that are a bit more interesting. Similarly for shoes; I tend to really not be keen on average brown / black - but blue suede was OK.

Obv not saying to wear those exact things, but if you have a look around you can find stuff you like a little even in styles you might not like over all.

I think it largely depends on context.

Then, clothing is a form of expression. It expresses an intention on how you want to be perceived (at a superficial level at least).

Regardless of style:

- Pick clothes that fit your size well.

- Some clothes may require some extensive ironing, especially shirts. If ironing is not for you, our you want to minimize your time ironing, have this in mind.

- Some clothes may not be able to be washed using home appliances and may require dry cleaning, etc.

- Colors and patterns matter can affect your perceived weight.

I sense an opportunity to build an AI generating clothing lines. At least for the buzz.
Try a clothing store with exact color hex codes on the tags of all garments, and, software in which someone's skin tone and eye color are matched with one's appropriate seasonal color. Such a store would diagnose/prescribe a shopper's acceptable colors and said shopper would choose items using the color hex code on the tags.

This could be an entirely online operation, too, given a smartphone app and a web store which provided access to the color codes for each of the garments.

See the book "Color for Men" by Carol Jackson for more details on seasonal color theory.

Send me a couple hundred if it ever gets off the ground.

- Start with the philosophy of having a few clothes of high quality rather than a lot of clothes of low quality.

- Fit is the most important thing. Get a few shirts and a basic suit made to measure. You can do this fairly inexpensively via sites like https://www.indochino.com/. I charcoal grey suit, a white shirt, and a light blue shirt are a great way to start.

- Understand the differences between style and fashion. Fashion is a never ending treadmill of mindless consumerism, constantly prompting you to buy new clothes. Style is about dressing timelessly.

- It's hard or go wrong with a nice pair of brown, leather soles shoes. I like Allen Edmunds: http://www.allenedmonds.com/.

- Read PutThisOn: http://putthison.com/tagged/Best_Of

"Nerds don't just happen to dress informally. They do it too consistently. Consciously or not, they dress informally as a prophylactic measure against stupidity." - Paul Graham
That quote may make sense in context, but dressing informally will certainly not prevent stupidity.
Indeed, and it could be seen as a form of conformity.

"Look at me. I'm not conforming. Just like everyone else."

It might be intending to express that informal dress keeps people overconcerned with dressing standards at bay. Informality is a refusal to compete.
- Get the basics/staples.

- Don't get any fad/trend items—i.e. ripped jeans are in (again) right now, but don't bother, just get a good pair.

- Fit means everything.

- Go for the 'uniforms' in the style you like (prep, street, or whatever).

- Quality over quantity (this is often related to fit).

- Dress to your body (not too tight or too loose).

- Honestly, just go to https://www.reddit.com/r/malefashionadvice/ and go through the sidebar.

- You can be incremental. Jeans are fine, just get ones that fit well, and get a pair in black. Swap the hoodie for bomber jacket or denim jacket. Get rid of your graphic t's and t's with slogans and 'funny' things.

- It doesn't have to be expensive at all. You can go to H&M or J.Crew for your basics (white/black/grey t's), maybe a button-down (oxford) or two, and a pair of navy chinos. Don't ever get jeans from brands that do lots of things (like H&M, Zara, etc.). Even if you do this, jeans don't have to be super expensive—Levi's have good fits, then there's other ones like Nudie's, Cheap Mondays, etc.

- Have some fun and experiment a little, but often you need to know the basics first to do this well (same for everything whether it be fashion, programming, art, or writing).

- You can completely skip getting someone who dresses well to help you out if you just aim to build a solid, basic wardrobe, and can shop by yourself.

- Always wear a belt. Get a simple tan leather one—you can wear it with navy chinos and shorts, black and dark blue jeans, etc. Get a simple watch. Go digital with a cheap Casio or analog.

- Don't overthink it. Just go for solid basics.

- Dress to your body (not too tight or too loose).

This also goes to things like stripes. If you're chubby, don't wear horizontal stripes. If you're short, wear vertical stripes to elongate you. If you're short wear waist or butt length jackets not long trenches. If you're tall, don't wear things that would elongate your lines, like wearing the exact same color through your shoes and pants. Silhouette is the term you're going to want to looking for in discussions.

- Honestly, just go to https://www.reddit.com/r/malefashionadvice/ and go through the sidebar.

+1 at MFA, but take it as a getting started guide on fits, and then once you get fits down, explore your own style. Check their WAYWT threads for lots of pictures of fits. You want to have a versatile wardrobe, not one with a ton of clothes that you can only wear with one or two things. I'm a huge fan of /r/streetwear personally with a touch of the flavoring of MFA (like collared shirts, polos, non perfecto leather jackets) and a bit of Americana like flannels and boots.

Also SHOES! Shoes are super important. I'm a sneakerhead, but if you're into more officey/professional vibe, Allen Edmonds makes some terrific shoes. Broguing on a shoe is more informal than not, a good cap toe in black and brown will serve you for a very long time. For boots, the MFA recommended Wolverine 1000 Mile and Redwing Beckmans are fantastic and can be dressed up or down.

Added an up-vote for previous comments about quality and fit. Both points are absolutely critical. To expand on those points:

1. Dress for who you want to be (and what you stand for) - I've found it helps to approach fashion the way you do your career. It's all about investing in where you're headed next. Your clothes are the first layer of who you are and if you think about it, it's awesome that you get to invent that every day. Pick a few things that feel like they reflect your identity (both current and aspiring) and go all out. Even if you don't dress like anyone else, you'll dress like you and more likely than not, that level of comfort will evoke a sexy kind of confidence.

2. Gather top-notch basics first - Grab yourself a nice pair of jeans and a white t-shirt that fits just right. Do a good job on this and already, you'll look better than most people.

3. Those basics will take you a long way - Stepping up your style game isn't about volume, it's about quality. Unless you're going for a dandy look or something to that effect, your approach to fashion should be aligned with the owner of a minimalist Tiny House. Everything you buy, from basics to accessories, should be beautiful, functional, comfortable and long-lasting (e.g. quality).

4. A versatile blazer or good looking jacket will take you everywhere - Find one or two that look sharp and feel comfortable. You want something that's as easy to turn to as your favorite hoodie. Speaking of hoodies, grab a nice sweater or two.

5. Eliminate barriers - Everything you buy should be as easy as possible. For example, buy non-iron dress shirts. That way you don't have the "I don't have time to iron" excuse for not dressing up.

6. Shoes maketh the man - Someone once told me every good man needs two things. An excellent bed and an excellent pair of shoes. If you're not in one you're in the other. Get some good comfortable oxfords and a pair of nice leather low-top sneakers (think Common Projects) for the weekends. Keep them clean, unless you're specifically going for a worn look.

7. Nice workout clothes make a difference - Odds are, you'll go somewhere before or after the gym. Invest in nice workout clothes. I spent years wearing my college athletic gear to the gym and thought it made me an "authentic athlete." Really it just made me messy, and the second I started investing in good-looking athletic clothes I realized it makes a difference. My new gear made me realize I should invest thoughtfully and opt for quality in everything I do.

If you're interested in learning more and want to talk menswear, message me. I'm obsessed with men's fashion and have done some makeovers for friends. Not selling anything here, just happy to help a fellow person who wants to be better.