This. Dear god, this. You don’t look good in that t-shirt with the ironic/sarcastic phrase on it. You really don’t.

My own personal advice, if you can handle shopping online, nothing beats the look of J Crew look for “nice casual” men’s clothing, and it doesn’t have quite the “I’m a douchebag” that A&F or some of the other mall places might have.

In no particular order…

If you’re not willing to invest in learning the rules and why fors of style, spending money is going to be a waste of money because you’ll likely invest in the wrong things, mismatched things, things you’ll fuck up by not taking care of properly, and you’ll probably fuck up the fit as well. If you actually want to learn some of the basics, the Details and the GQ yearly style guide for men are actually pretty good at making you dress somewhat trendy while avoiding coming off as douchey/trying too hard.

Clothing is about the image you’re portaying and the tribe you want to identify with. If you don’t have an idea of how you want to come across, then you’ll likely end up looking awkward.

If you buy clothes you’re not familiar with, you’ll look awkward. A guy in a $5000 suit who doesn’t wear suits will not look as good as a guy wearing a $250 suit but wears suits all the time.

Don’t buy clothes that you don’t know how to take care of. There’s no point in getting a shirt that requires ironing if you can’t iron; don’t get a nice wool coat only to have it moth eaten in a year; don’t get dry clean only if you don’t use a dry cleaner; don’t shop at all if you can’t be bothered to separates lights from darks and know when to wash on cold.

Style is ever lasting, fashion is ephemeral. James Bond has style (ignoring the Roger Moore era). Skinny jeans are a fashion.

FIT MATTERS MORE THAN ANYTHING ELSE. An ill-fitting Prada shirt is going to look worse than a properly fitting Old Navy shirt.

DON’T INVEST IN TRENDS. If you want to spend $200 on classic wash, classic fit Diesels or Sevens, that’s fine – that’s an investment. Spending $200 on skinny fit jeans or super distressed jeans or super pointy toed shoes is going to be a waste of money (if you toss them when they’re no longer trendy) or embarrassing (because you’ll keep wearing them in two years).

There are a lot of subtleties to putting together an outfit that can torpedo your general aesthetic if you’re not ‘trained’ up on this. How your collar sits, amount of cuff to reveal, how your pants sit/ride, whether your belt is too long, tie length, shoe choice, pant length, even which buttons to button, color matching, how baggy/tight your clothes are, and many other factors.

Understand how certain clothing is a no-no based on your complexion and body type. Thick, squat neck? Avoid turtlenecks. Ruddy complexion? Avoid red tones. Super fair skinned? Avoid washed out neutral colors. Short and stocky? Avoid double breasted suits. Tall? Stick with 3-button suit jackets.

Know where to shop based on your ideals. Don’t shop at American Eagle, Hollister or A&F if you’re in your late 30s. Know that in general the stuff at Jos A Bank and Brooks Brothers are targeted at people in their 50s. Barneys is where you go for clubbing gear.

Don’t be that guy that’s wearing clothes for someone 10 years younger than him.

Don’t wear clothes in an attempt to show interesting you really are.

A message board isn’t going to be the best place to learn how to do this right, but hopefully you can see how there’s a high risk of doing it wrong if you’re not going to get educated on the subject.

The goal is to come off with a look or style that looks effortless and natural. The minute someone notices what you’re wearing, you’ve already partly screwed up. It should be an extension of your personality and it does require care and effort just like any other grooming.

And again, spending more money in the right hands can reap dividends, but by and large knowing how to shop for clothes period is a much more valuable skill.

People giving you “let women pick out your clothes” are seriously misleading you. Most women, like most men, have bad taste in clothes. Women who have good taste in clothes often really only have good taste in women’s clothes (and there are big differences - for example, business-y clothes for women seem generally of a much lower quality than for men for similar prices). But women are often socialized into thinking they have good fashion sense because they are women. It’s sort of like picking a stock broker - most can’t pick stocks to save their lives, but neither can you; they get customers by being confident. If YOU don’t have good fashion sense, you are likely to be convinced by a woman’s self-confidence that she does, whether or not she does. On the other hand, you are somewhat better off with a guy who you think dresses well and who thinks a lot about clothes. They are a bit more likely to understand men’s fashions.

If you are married, then it makes more sense for your wife to shop for you, since you are to some extent trying to dress for her, not necessarily to dress well.

Gabriel Hounds denim. The only way to go.

I cannot stress this enough. Also: the trend of pre-distressed jeans drives me bonkers. I had a gift certificate that someone gave me to Lane Bryant, and I went in just trying to find “basic” denims and it was almost impossible to find underneath all the piles of pre distressed denim. Besides, fat women (and yes I am one!) shouldn’t be wearing distressed denim anyway, makes them look like there’s been an unfortunate accident. :P

Goddamn, a lot of posts while I was typing up my epic post from hell.

Re: T-shirts. There’s a point of diminishing returns, which for me is at around $15/shirt. The difference between a nice Gap fitted T and a cheap Hanes is pretty substantial, but the difference between that Gap and a high end D&G T-shirt is almost non-existent. Gap has GREAT T-shirts. I stock up whenever they’re on sale – and they’re available in lots of colors and lengths (including ‘Tall’ sizes).

Re: jeans. It’s not just about quality, but about fit, and if you’ve never had jeans that fit properly it’s hard to really understand what the big deal is. I have some very nice Sevens that are way too loose since I’ve lost weight, and my Citizens that I bought on sale for 1/2 the price are way, way nicer because they fit better.

Re: J-Crew. Yes. Very good casual fare that is a little high priced. Surprising how expensive some of their stuff is, often venturing into boutique/premium areas.

There are weird subtleties too. For example, for those guys that have had a, uh, unsightly bulge in certain jeans – that’s actually due to the upper legs not fitting properly. The fabric gets pulled at the hip, which leads towards the bulge. Proper fitting jeans don’t have that bulge. And don’t have jeans that sag on your ass.

Men and women have opposite psychoses when it comes fit. Men tend to err on the side of baggy, thinking it’ll hide their paunch – it doesn’t, it just makes you look slovenly and shapeless. Women tend to err on the size of too tight, because they often get in size denial (“I am NOT a size 10!”)

Fit should be like revenge. Precise and merciless.

Forget shopping with the girls. Go shopping with a gay male friend who has some style of his own. It’ll rub off. Bring $$$.

Get a few classic pieces and the rest will fall into place. Linen always looks good for some reason, at least in the warm months. Solid, textured fabrics are always a better buy than stripes or patterns in shirts. Earthy tones will always be in fashion, khaki, hunter green, darker blues, maroon rather than red, sand rather than yellow. Leather will never, ever go out of style, nor will silk.

I’d say my favorite pieces of clothing are a casual camelhair jacket, a handmade primitive leather belt, a wool overcoat, and various sport/casual shirts in solids. With black pants I tend to wear red and warm green shirts, with lighter khaki I wear lighter green or brighter yellow (no yellow that would be close to the khaki) or white. With jeans I usually go for an untucked camp shirt, but I’ve grown fond of wearing courduroy instead of jeans casually.

My point of reference is usually what the Clooney set wears on vacation. Natural fabrics in classic styles and muted colors lets me be comfortable, and that makes you look all the better.


Jeans are lame. They’re uncomfortable. They exist to cling to your legs and ass, and I would prefer clothes that don’t show off my fat ass. (Okay, it’s not that fat of an ass. I still don’t like jeans.)

Cargo shorts when the weather is warm enough, slacks otherwise. I buy my clothes from Banana Republic for a reason; I can walk in there and, fifteen minutes later, walk out with exactly what I wanted in sizes that fit me precisely off the rack, and if they happen to not have something, they’ll adjust it.

For a top, I like simple t-shirts or geekery. This is exactly the kind of geeky shirt I approve of. Otherwise, I’m most likely to wear a black t-shirt of some sort (I have a number of them; the Outward Bound shirts have the highest fabric quality) or a solid, dark color like a dark green or dark red.

For going out, I might wear a polo shirt. For formal occasions, I have suits and even a tux, but that’s not dressing/fashion, that’s High Fashion ™, and is a completely different story.

And yes, this here geek gets laid wearing that sorry excuse for fashion. Take a hike, popular fashion; I bid thee pass me by.

Are we going shopping? Ha ha. Sorry, I don’t have any male gay friends. Need to start hanging out in Dupont for brunch more!

If I had a Lotus I’d have no need for all this fashion nonsense!

Yeah some of the stuff at J Crew is pricy, but if you’re buying foundation pieces it can be worth it.

Another thing about sizes. Different stores and different brands have different sizes. I used to think this was just a women’s clothing problem, but I read an article in Esquire about it recently that it’s creeped into men’s clothes too.

Another thing: before you try to figure out what style you are, experiment with different looks. That way you don’t over invest in something like polos or khakis then six months later decide you hate the feel/look.

The easiest way to get experiment is to think of someone that dresses well or look through a GQ or Details or whatever and then try to emulate it at a lower price point.

That said, most places that target men understand that men are confused, so they try to display premade outfits for you to just look at and go “I want to dress like that!” Then roll with that and see how it goes.

Express is a surprisingly good place to shop if you want generic clubbing gear and you’re young enough (or apathetic enough) to pull it off. Their Modern Fit button downs are available in a wide variety and their savings stack ridiculously well.

When asking for advice from an IRL friend who dresses well, make sure they’re trying to dress YOU well vs. trying to take their own style and push it on to you.

And shoes really tie it all together. Make sure you have the staple dress/business shoes and casual shoes and know when to wear them, and then just figure out what kind of casual shoes appeal to you for general milling about (loafers, Sperrys, Vans, Chucks, sandals, etc.)

Honestly, I think a simple error a lot of guys make when it comes to fashion is that they don’t look at other men with an analytical eye. When you go to work, just look at people; what are they actually wearing, what is their posture, do you get an instinctive positive or negative feeling when you see someone?, why?, look at their shoes, which colours and types of clothes they’re wearing, and so on. Since you’ll see a hell of a lot of people any normal day, it shouldn’t take someone who can nitpick a movie to death that long to get a fundamental grasp of what works.

Fine words, sir, but with limited application for people trying not to spend teh big buxx on their wardrobe.

Then again, I’m just now starting to get rid of (I stopped wearing them a while ago, but I mean actually physically donate and get out of my closet) some of the sweaters I’ve been wearing since middle school.

For now? Thrift stores. And I’m not advocating hobo chic; I’m advocating an already-broken-in pair of jeans, a couple of decent button-downs that work either entirely closed up or draped over a decently tight T-shirt; and, who knows, maybe even some cute accessories. Goodwill’s a weekend adventure when you’re twenty and going with someone.

But don’t do as Aaron half-seriously proposed and shop for all of your clothing needs at such a place. Used slippers? Years of someone else’s feet-stank? For that, hon, it’s worth the trip to Target. :P

Most dangerous out-of-context phrase to quick-read EVER.

The best white t-shirts I’ve found are Calvin Klein 365. At $30 for two, they’re not cheap, but I defy anyone to tell me they’re not worth it.

I have two gay friends and neither one of them can dress for shit. It’s so disappointing! One of them has a plaid, pastel, corduroy shirt. Where do you even buy those?

Well, not necessarily.

I was recently talking with a fashion-obsessed friend about fittiness recently. I was wearing a leather jacket that I said was too small, since if I buttoned it up, it did not drape in a clean line, and he insisted that it actually fit correctly, since a leather jacket should be… not skin-tight, exactly, but not like a wool dress coat, either.

He went on to opine that pretty much all my clothes were actually too big/loose, and that I should wear things that were more fitted. I brushed him off as insane, because HONESTLY NOW, the last thing people want to see is tight clothes on a fat dude.

But on a whim, I did pull out a smaller shirt from my closet and tried it on. It felt REALLY tight, in that it conformed to my torso instead of just hanging loosely around it, but when I looked at it in the mirror with a neutral eye, I’ll be damned if it didn’t actually look a lot better.

So yeah, there’s a money aspect to things, but there’s also a certain amount of just being aware of what good fit is. And probably most of all, there’s a time aspect to it – if you’re the sort of person who says “I wear 34x30 pants” and then you walk into a store and buy a pair of random 34x30 pants off the shelf on the basis that they fit, you’re kinda scrod. You need to actually get in the habit of trying things on to be sure that they fit for real, as opposed to just looking at the size on the label, because there are any dozens of ways in which clothes can fail to fit that measurements won’t tell you.

You can find clothes that fit well at Target and Wal-mart. The issue of fit has more to do with understanding how certain designers and stores design their clothes (their archetypes) and how your own body fits into their model than it does with cost.

And then finding a tailor that can take your purchase and make it fit properly. Get your pants hemmed, your sleeves adjusted, your shirts taken in, etc. This stuff isn’t that expensive and you look a million times better when your cuffs aren’t going all the way to your palms, your pants aren’t dragging, and your shirt isn’t blousy and/or bunched up in the center of your back.

Pro-tip – you can’t really adjust waist sizes on pants more than about 2" without having it look awful unless you do a full recut, and that is expensive as hell. As tempting as it may be to get someone to take a 36" to a 32" if you lose weight…just buy new pants.

I think the biggest trick is to shop more often. Or at least browse more often and maybe try a few things on without the intention to buy anything necessarily. What’s in a lot of clothing stores changes all the time and sales can now be found on men’s clothes that are almost as deeply discounted as on women’s clothes.