How to dress like a man.

July 4, 2010 9:07 PM

Help me dress like a grown up. I'm tired of looking boyish on days that I don't wear a suit and a tie. What can a wear out around town, doing errands, at restaurants that says "Yes, I am an adult. Yes, I care about the way I look. No, I didn't wear this to work."

Polo and khakis = either food service or frat boy.
t-shirt and jeans = I don't care what you think about me.
athletic gear = I care way more about me than I ever will about you.

What am I looking for?

posted by Drama Penguin to clothing, beauty, & fashion (35 answers total)

Put This On - A podcast and informative website on dressing like a grown-up.

A t-shirt and jeans isn't so bad, though, as long as it's a nice t-shirt, and good jeans.
posted by SansPoint at 9:16 PM on July 4, 2010 [2 favorites]

I know you said "suit and tie" but I am a huge fan of an oxford shirt paired with a fun/colorful bow tie.
posted by makethemost at 9:37 PM on July 4, 2010

I like to subscribe to what I just decided to name the One Stylin' Principle. The basic explanation is you take one item of your clothing and go all-out, but leave everything else normal. So, jeans and a t-shirt but some nice black leather shoes. Or, jeans and sneakers but with a fitted button-down. The idea being, Yes, I'm comfortable with what I wear, but I am going to show you that I do actually possess the shared cultural norms to look good were I to decide to do this all the time.
posted by Civil_Disobedient at 9:40 PM on July 4, 2010 [12 favorites]

as long as it's a nice t-shirt, and good jeans.

I totally agree with this. Good jeans and good shoes.
posted by cabingirl at 9:41 PM on July 4, 2010 [1 favorite]

I'm a big fan of guys wearing a nice pair of jeans and a well-fitted button-down shirt with rolled up sleeves. Sort of like this or this. It's casual and yet pulled together at the same time, and is much more grown up than a tshirt.
posted by pecknpah at 9:42 PM on July 4, 2010 [8 favorites]

Throwing a nice blazer/sport coat over a tshirt and jeans really elevates a look. Good shoes, of course. Good shoes always make you look more grownup. Not runners, proper shoes.

Also, accessorize. A nice chunky bracelet on a man, I find, is both grownup and sexy. Dunno why.
posted by dirtynumbangelboy at 9:50 PM on July 4, 2010

I sympathize - this is in many ways easier for women than it is for men*, but:

1. Nice shoes. This is probably the biggest thing.
2. Jeans are fine, so long as they're nice jeans. Go to nice stores, go to vintage places, try stuff on - there are some very nice, very classy, very attractive jeans out there. There are also things like chinos that can look great in a more casual style.
3. In general, things that fit and that aren't threadbare.
4. For tops, honestly? You just have to shop. Again, try things on. Stores will have a huge variety of shirts that don't fit into the standard work vs. t-shirt vs. club shirt trifecta, so you'll just have to go looking. Sportcoats are great if the weather allows (spring/autumn).
5. Questions like this are why publications like GQ exist. They are, in many ways, noxious, but you can definitely look through the pictures for looks that you like. Try to figure out what's going on in those pictures.
6. Accessories. For men this principally means "a nice watch that matches the outfit", but things like hats, belts, other wrist accessories, etc. can and do all help. And honestly, the confidence to pick out and wear a masculine necklace for yourself is kind of rare, and I feel like it makes an impact for that reason.

The more money you have to spend on this project, the easier it is. It's possible to look great on a budget, I've seen others do it, but I've personally never really managed it.

*Please do not be mad at me, women! I know that appearance/fashion can be its own hell for y'all. Women, however, have access to the dress, and there is just nothing that men have access to that can match the casual, fun fabulousness of a dress in the summer.
posted by kavasa at 9:51 PM on July 4, 2010 [5 favorites]

Definitely make sure you have nice shoes! White sneakers make anything look more casual, and not in a good way. If you need to have sneakers, at least try for some sleek black ones or something. New Balance shoes may be comfortable but they don't scream (or even whisper) style.

Properly fitted jeans that aren't riding too low are also good. The ladies (okay, maybe just me) prefer to be able to tell that you have something back there, and the baggy (or really low) jeans do not help with this. Pair these well-fitting jeans with an untucked dress shirt in the style that pecknpah suggests.
posted by that girl at 9:54 PM on July 4, 2010

I know some keeblers who roll in button downs with the sleeves rolled up and nice jeans, and somehow they still manage to fit in with the kids I know who wear brightly colored skinny jeans rolled up to right under the knee or American Apparel everything or girls who look like Rainbow Brite threw up on them (me). It really is a combo that can take you anywhere; you simultaneously ready to go be a classy grown-ass adult somewhere OR drink Tecates in a parking lot with your kith and rock drunk pisses in the alleyway behind people's houses.
posted by Juliet Banana at 10:10 PM on July 4, 2010 [7 favorites]

nthing good shoes. It just sets the bar.
As for other, just go to J. Crew. For some reason, their stuff just looks a little classier, even when it's casual. Buy or don't buy, but check out that style, cuz it's a mutha.
posted by Gilbert at 10:13 PM on July 4, 2010

I would recommend straight jeans with a dark wash, something like this. If you want to go more casual, lighter jeans can be okay too, but make sure they fit well.

On top, if you want to go more casual, in my opinion a v-neck looks good if it fits you right, something like this. Graphic tees can also look fine if they fit you correctly, are in good shape, and don't have too out there or inappropriate designs, like beer logos or naked women.

If you want to dress up a bit more, I like sweaters or button shirts, preferably with the sleeves rolled up. Try this, this, this or this. You'd want to wear these over some sort of undershirt.

If you're just wearing a t-shirt, I'm partial to a classic, well fitted hoodie, like this. I wear them halfway unzipped, with the sleeves pushed up.

This page has some nice suggestions for what types of shoes to wear with jeans in different situations.

(Note: I used Gap for my examples just because the type of stuff you're looking for is pretty easy to find there, but there's loads of other places for you to look as well)
posted by kylej at 10:23 PM on July 4, 2010 [2 favorites]

Good advice so far up thread. My personal opinion: never wear polo shirts unless you're golfing. If you feel the need to wear a polo a short sleeve button down is always the better choice.
posted by sockpup at 10:46 PM on July 4, 2010 [2 favorites]

My two basic paths are:

Jeans, fitted dress shirt, sleeves rolled up if it's hot out. This is my "summer date" uniform. Look for lightweight shirts - linen, for example - that will handle the heat better.

Alternately, jeans and carefully selected t-shirts. Perfect fit, awesome designs. I almost exclusively wear jeans (long) and t-shirts during the summer, but I like to think it's pretty clear that they're t-shirts I give a crap about. No random faux-70s stuff, or boring shirts they gave me for a volunteer weekend; my t-shirts are artsy and a little weird and very Me. Not that everyone's constantly stunned by my amazing t-shirts, but I do regularly get compliments on them. It probably helps that most of my shirts are relatively unusual - not that Design by Humans, or Teefury, are particularly exotic websites, but it's a damn sight more unusual than something that you saw at Urban Outfitters.

I say this as a guy who doesn't like looking boyish; left to my own devices, in cooler weather, I pretty much exclusively wear dress shirts and sport coats, often with a tie if the event permits.
posted by Tomorrowful at 10:48 PM on July 4, 2010 [1 favorite]

dress like this guy from The Sartorialist blog
posted by fifilaru at 11:13 PM on July 4, 2010

3. In general, things that fit and that aren't threadbare.

This. Gene Kelly wore polos and khakis. Marlon Brandon wore t-shirts and jeans. Everybody should develop their own style; looking like an adult is more about wearing clothes that fit properly and are in good shape.

Most people (me included) are initially terrible at judging their own size. Go to a tailor and get measured. Write all that info down on a card and carry it around. Find out what kinds of clothes (color and style) you like. If you wear clothes in the right size that reflect your personality and style, you will look like an adult.
posted by chrisulonic at 2:31 AM on July 5, 2010 [2 favorites]

I sympathise with your question and the fact that it takes effort to do this day in and day out (I'm not quite there yet).

I think kavasa's list has everything you need to know. Particularly point 5 - we can all tell you what works for us (I'm a big fan of linen pants, light polo's or shirts, loafers) but really you should grab a few magazines and tear out anything that looks good to you. Then go through all of those and try to figure out what you think would work for you and what is basically going on there that you like.

Once you've got it together, you will "look marvellous" which will make you feel marvellous, which is what it's all about right?
posted by HopStopDon'tShop at 5:44 AM on July 5, 2010

I'm a big fan of a button down shirt with a sweater over it. (In the fall/winter, anyway).

It's probably really obvious but no matter what you wear, if it doesn't FIT, it will look bad and you will look sloppy.
posted by joeyjoejoejr at 8:03 AM on July 5, 2010

Well these days everyone in London is wearing proper buttoned shirts and jeans, with either sneakers or vintage leather shoes.

T-shirts seem a bit 'out' in a way.

Also uf the shirt is dark coloured it generally doesn't look like something you'd wear to work.
posted by mary8nne at 8:09 AM on July 5, 2010

Speaking as a woman who looks at men, I think the way to say ""Yes, I am an adult. Yes, I care about the way I look. No, I didn't wear this to work." with your clothes is entirely: fabric, fit, cleanliness and care. Doesn't matter whether it's jeans & t-shirts, cargo pants & henleys, slacks & button-downs, suits or whatever. If it's hanging off your body, or frayed, or faded, or holey, you look like a kid who doesn't know better, or doesn't care. If it's appropriately fitted and well-taken care of, you look like an adult. Basically, what kavasa said.

A guy in ratty jeans with two inches of boxers sticky out the top in an over-sized t-shirt with something (anything, really) printed on it and flip flops looks like a kid who doesn't care. A guy in jeans that don't ride down in a heavier-weight t-shirt (which hasn't faded, pilled or stretched from wash & wear) with no slogans looks the opposite. Personally, I like solid colors with nothing on them in a t-shirt because I think anything at all, no matter how clever or well-designed, on a t-shirt looks like silly. Obviously, people will disagree, which is why I say "no slogans": to distinguish from designs. There is a difference between a nice design on a t-shirt and something you got free for volunteering or picked up at your first concert. Sure, there's a time and place for your favorite band t-shirt, but it's not how you telegraph that you care about what you're wearing.
posted by crush-onastick at 9:04 AM on July 5, 2010 [6 favorites]

This is something that requires real research and honesty and I applaud you for recognizing that you'd like to look like a man, not a boy. I would also recommend checking out putthison.com for a good starting place. Some of their advice is a little too dandy for me (like tie-bars and bow-ties) but they know what they're talking about. Find other men's style blogs and see what's out there.

If you want to dress like a real adult and give off a good air of maturity it is essential that you avoid:

*graphic t-shirts - pictures are for kids...always go plain
*sneakers of any kind unless playing sports
*any pre-ripped jeans or anything similar (always go dark)
*untucked dress shirts with the cuff rolled up once that makes you look like a contestant on American Idol or Jessica Simpson's father
*skinny jeans
*cargo pants
*white socks
*hoodies
*Old Navy

These are all fine for 21-year-olds, but not for men. Most of these will work against you, in my opinion. Rather, try to acquaint yourself with:

*good chinos, no pleats
*some good button-up shirts
*a good blazer
*brown shoes
*a good tailor
*some nice, simple ties - narrow is fine, but try to avoid skinny...too fad-ish
*Banana Republic
*Lands' End
*Brooks Brothers
*J Crew

And keep in mind that you will get what you pay for. It's better to have one pair of great jeans that cost $150 than three cheaper pairs that cost $50.
posted by fso at 9:14 AM on July 5, 2010 [1 favorite]

I like when guys wear non-khaki, non-jean more suit-ish (but not quite that formal) pants. Think old man or grandpa pants, modernized. My guy has made the switch recently and I love it. It's a bit of a balancing act though--the easiest (read: laziest) way to coordinate it is with simple modern sneaks, a casual cotton shirt (t shirt ok maybe) and casual blazer or jacket, but obviously this will give you a certain nerdy hipster Rivers Cuomo-y look that may scream boyish and too young and college-y to you, as you've already pointed out other outfit connotations. But I think if you play it right you can avoid that if you wish--wear a sleeveless sweater or something gently preppy but modern with it and said simple sneaks or otherwise quiet shoes and maybe you'll strike a balance of looking grown up without looking Polo Lauren or Abercrombie douche-y. And if you're trying to do this on a budget, depending on your dimensions it's laughably easy to get said pants at thrift stores. They really were your grandpa's pants, so.

The polo thing...it definitely does have the connotations you mention, but played right if you're already totally against that fratty type it still looks grrreat. Yes, I am admitting my weakness for polos on guys. They tend to be the one shirt men wear that gives you a sense of their chest, that isn't so loose it hides the body, maybe that's why. Sigh. As long as your collar's not up and you're not sporting a fake tan or highlights or spiky hair gel 'do or (shudder) a visor maybe you're doing ok.

You could also try a '60s NASA flat-top coke-glasses science-y nerd thing, with a white shortsleeve oxford button down shirt, dark pants, and a tie. You have to tread carefully here there though to avoid the "Mormon with a bicycle helmet" connotation...but I've seen guys pull this off occasionally and when it works it really works.
posted by ifjuly at 9:21 AM on July 5, 2010

Also, when it cools down some, corduroy jeans on men=so cute.
posted by ifjuly at 9:22 AM on July 5, 2010

You can wear a pair of nice jeans like a pair of 867's from Ralph Lauren and a button down shirt like this. Just wear it with a a nice Swiss automatic watch and a nice but not dressy pair of shoes like these Havana Joe's 0202's. Put on a navy blazer, swap the 0202's for a pair of Tod's driving shoes and you can go anywhere.

That's grown-up without looking like you're trying too hard.

Stick with the basics (including basic colors) and remember that it's the little things that make some men look like they're clueless (flip flops with jeans or any pants, wearing flip flops in public places other than the beach, wearing too many colors, not wearing a proper timepiece, etc.. ) With the exception of Polo and Lacoste, avoid logos on anything. And even with those two brands, only on their basic polo shirts.

And if you want to look mature, don't try to dress on the cheap.
posted by L'OM at 9:56 AM on July 5, 2010

If I'm going for what you're going for, I generally wear buttoned shirts, untucked, paired with casual (flat front) pants. In colder weather, I'll wear a turtleneck or mock-turtleneck.

Personally, I think as other people point out, a lot of this hangs on the shoes. Jeans and a tshirt with a decent pair of shoes says, "I am an adult going about town on my day off." With a pair of sneakers, it says, "I am a 12 year old."

I personally think that going around in a blazer when not otherwise doing something "nice" starts to come off as an affectation, but my standards of dress tend to be more casual than others.
posted by deanc at 10:27 AM on July 5, 2010

If you feel the need to wear a polo a short sleeve button down is always the better choice.

A short sleeved button down shirt is never the right choice. Never ever ever.

Never.

Just roll the sleeves up of a normal shirt.
posted by djgh at 10:35 AM on July 5, 2010 [7 favorites]

A short sleeved button down shirt is never the right choice. Never ever ever.

Agreed. It's unbelieveably uncool. There's never an occasion for it.
Cases in point
posted by fso at 10:48 AM on July 5, 2010

Yeah, obviously don't wear a short sleeve DRESS shirt.

But short sleeve sport shirts are fine.

And white sneakers can look great if they're something like Jack Purcells.
posted by mullacc at 11:18 AM on July 5, 2010 [1 favorite]

Depends a lot on where you live and what climate you have. In my our hot, humid Houston climate, I like Cubavera-type stuff, not necessarily the guayaberas (unless you can pull it off well) but the lightweight sport shirts with light linen pants or shorts. I see this sort of thing from them and other companies at local department stores (Macy's, Dillard's) as well as mid-range stores (Kohl's, Palais Royal, etc.) It's important to feel comfortable if you're going to act comfortable and confident.
posted by Robert Angelo at 1:20 PM on July 5, 2010

Was it on MetaFilter that someone brought up Nerd Boyfriend? As a young lady, I've actually learned a lot about men's fashion (and men, in general) from this site. It can be a little 70s centric, but, um, I love the 70s and I think it does a good job of both celebrating and then demystifying (by showing the constituent elements) a great outfit.

"You'd want to wear these [button-down shirt] over some sort of undershirt."

Not necessarily. I live in Paris; one of my favorite French dudes' fashion ticks is the absence of undershirts. To me, there's something oddly grown-up and very sexy about it. I mean, the shirt itself should be good: quality, fit, etc., but it's really working for these guys.
posted by delayed-reaction android at 2:00 PM on July 5, 2010 [1 favorite]

I'd like to put forward a note against Put This On. It's a good place to start when it comes to 'looking like a grownup' (whatever that means), but I eventually grew to dislike the site as it is more concerned with what is 'correct' rather than what looks good. Quite a bit of the advice directly contradicts some of the more fashionable people featured on The Sartorialist.
posted by slimepuppy at 2:17 PM on July 5, 2010

In the summer, a nice linen suit could be what you are looking for.
posted by clark at 8:10 PM on July 5, 2010

Ben Sherman shirts and nicely fitted designer jeans without gratuitous washing or fake wear (I prefer Citizens of Humanity, Hudson and William Rast) work out well for me. Nth-ing what everyone said about having some nice accessories (watch, chunky bracelet) and wearing good shoes (though I believe that the black, Converse all-star low is a timeless classic for all ages).
posted by brand-gnu at 8:51 AM on July 6, 2010

Oh, and if you wear glasses, have a few different pair. Ones that say "I'm all business" for the office and ones that say "I'm not a stuffy office drone" for your days off.
posted by brand-gnu at 8:52 AM on July 6, 2010

I'll add boat shoes for that summer out-and-about vibe. Be careful to get ones with real leather all the way around (they breathe.) Don't wear socks, but do give them a dose of baby powder before you put them on.
posted by ChurchHatesTucker at 9:34 AM on July 6, 2010

Any button shirt takes you out of the teenage look instantly (unless it has METALLICA!!! printed on it, of course).

Chinos, dockers, khakis, nice jeans, leather-look slip-ons, no bracelets (but necklaces & earrings are adult), but most of all, button-up shirts. You can find fun, bright, interesting, and cool/warm shirts for any occasion; none of them say "I'm not ready to pay my way yet!".
posted by IAmBroom at 6:59 AM on July 7, 2010