dude in shorts
May 2, 2013 9:22 AM   Subscribe

It's warm weather season. I want to wear shorts, but I also want to up my style.

Firstly, all my shorts now are cargo shorts. When I'm wearing these, what else should I wear with them to up my style / minimize dorkiness? Specific shoes, shirts combos? something else?

Secondly, my understanding is that minimizing my dorkiness in the first question is hindered by cargo shorts. So, if I'm buying new shorts, what sorts of things should I look for? In the last questions about men and shorts, there was a wide variety of argument as to what everyone liked and thought was stylish. Is this a case of varying by region, or is there this much disagreement in style?
posted by garlic to Clothing, Beauty, & Fashion (33 answers total) 26 users marked this as a favorite
First of all, Husbunny wears shorts to work every day in the warm months. He loves them!

I get him knee-length shorts, flat front and usually with a madras or plaid pattern. Then I match his polo shirts et voila! Garanimals for adults.

I got him a pair of Izod shorts, white with navy blue lobsters on them. Pennys and Macys have them. Matching Lobster shirt is adorable.

Cargos are okay, but they tend to look dumpy. Iron them and pair with a nice short sleeved, button down oxford. If you really want to go GQ, do the Cricket vest.

The Sperry Top Siders with no socks is good for the office. Flip-flops are fine if the feet don't look like they're tree trunks (a manly pedicure is a GOOD thing.)

Preppy is the way to go. Study Tommy Hilfiger and Ralph Lauren look books.

posted by Ruthless Bunny at 9:37 AM on May 2, 2013 [1 favorite]

Best answer: Engineer giving fashion advice warning:

To the first question: if "minimize dorkiness" is desirable, forego the Half-Life T-shirt & anything you got on ThinkGeek, in favor of plain T-shirts, polo shirts, short-sleeve button-front shirts, etc.

Second: Plain shorts. Pretty much cargo shorts without the pockets, maybe a little more refined cut. On both the shirts & shorts, I have good luck in the J. Crew ballpark, though your taste may vary.

posted by jeffjon at 9:37 AM on May 2, 2013 [2 favorites]

I personally like almost all of these rather pricey J Crew shorts, with the exception of some of the more exuberant ones.

I like them because they fit neatly rather than being baggy. They are tailored. They don't have extraneous loops, tabs, pockets, etc that distract the eye, catch on things and are not actually in use. They can be belted, and they will go with most kinds of belts, not just the very casual sort that you'd wear with cargo shorts if you wore a belt at all. They hit the leg at a good point - cargo shorts tend to hit in the middle of or right below the knee, or even at the widest part of the calf, and this breaks up the line of the leg. Just above the knee or low-mid-thigh looks best. They are comparatively classic - you could wear them five years from now, or could have worn them in 2007, and not look particularly out of place.

(Now, I think there are ways to look good in cargo shorts - just that it's a higher-level style approach than one customarily takes.)

With such kind of shorts? You can't go wrong with a not-too-baggy but not-too-tight tee shirt in a plain color that suits you. Shirts that advertise things are deprecated unless they have lots of meaning to you personally. Shirts that try to impress an audience are also deprecated - even if you just love the NYT book review, you don't need a shirt that shouts this. I am not a fan of logo shirts in general. Stripes are okay although getting, sadly, a little too universal.

With tee-shirts, fit is important. It needs to be intentional. I saw a guy in a really loose, baggy shirt the other day, and it looked great - because he had picked a loose, baggy fit that looked good, not just grabbed a rando tee off the rack at Target.

Really, I tend to wear shorts and a lightweight collared shirt with the sleeves rolled up. Short-sleeved dress shirts can be very dapper/fashion-y, but they aren't my thing. Honestly, if the weather is below eighty, I wear lightweight pants rolled at the ankle.

Shoes? Should be intentional. I saw someone the other day in shiny purple ones, looked fantastic. Classically, canvas ones in colors that look good with your other favorite colors.

So I might wear, for example, dark blue shorts (that are really cut down, hemmed cords I originally got on the Target sale rack) and either a grey tee shirt or a light blue button front with the sleeves rolled. I might wear light brown loafers, blue suede oxfords, blue canvas slip-ons, grey canvas lace-ups, etc.

Most of my clothes are different blues, brown, grey and beige, so I tend to buy stuff that coordinates with those things.

Basically, your clothes should look like you intentionally picked them out, not just raced in to Target and grabbed the first thing you saw. They should fit. They should not have details that you never use - ie, cargo shorts are totally awesome if you actually need the pockets, but if they're just flapping emptily around your knees all the time, it just seems affected. They should not have lots of logos! and branding! They should not give the impression that you want everyone to know how radikewl you are, because that just looks kind of dumb to everyone outside your immediate social circle, and it looks dated really fast.
posted by Frowner at 9:45 AM on May 2, 2013 [4 favorites]

Seconding flat-front shorts as your best option. I'd avoid the patterns unless you're sure you can carry it off - khaki is the super safe option. A linen button-down is a nice casual look, though a regular button down with the sleeves rolled up would look nice as well. And yeah, to be more polished you have to skip the statement/cartoon/nerd pride t-shirts!

For shoes you can definitely go with the top-siders look, or I think any type of low profile sneakers like pumas can be good. Adidas has some nice options too.
posted by brilliantine at 9:46 AM on May 2, 2013

No pleats.
posted by something something at 9:46 AM on May 2, 2013 [6 favorites]

Cargo shorts are too adolescent to clean up; get these 7" Stantons and roll 'em up once, or the 5" version and let them be. You might also have luck finding some soft, slim, flat-front shorts at Gap right now.

Fit guide: ensure they make your butt look good (bring a friend if you need to), and that the outseams don't flare or diverge too far from the line of your thigh.
posted by a halcyon day at 9:46 AM on May 2, 2013 [3 favorites]

Best answer: Cargos are okay, but they tend to look dumpy. Iron them and pair with a nice short sleeved, button down oxford.


No, do not ever wear a short sleve oxford shirt. Just no. And for the love of all that is holy, IF you MUST wear cargo shorts...iron them? WTF. Ruthless Bunny, I usually dig the things you say, but dear lord. That's a dork uniform right there. (You can wear this if you want to look like a child who got lost on the way to the school bus stop...and as you are a shorter fellow, I can't say I recommend it.)

garlic, I grew up in the south, which is the Land of Men Wearing Shorts and Looking Nice in Them. I can't say I fully condone the practice (looking nice in shorts almost requires you to look preppy, but unless you're gonna run around pantsless in the summer heat, I suppose it must be done).

The trick is to get shorts that hit above the knee (not, like, wildly above the knee, but enough that you can actually see that knees exist in there). And some sort of low shoe with no or no-show socks.

Flat front, fitted (not tight, but such that they look like this more than they look like this--you don't want to be swimming in the things).

Seersucker is great and super lightweight. And in general go for fabrics that look more lived in--that'll look put-together casual. That sort of shiny fabric like what you find on slacks will make you look like you're trying way too hard to be a guy who wants to look nice in shorts.
posted by phunniemee at 9:52 AM on May 2, 2013 [17 favorites]

No, do not ever wear a short sleve oxford shirt. Just no. And for the love of all that is holy, IF you MUST wear cargo shorts...iron them? WTF. Ruthless Bunny, I usually dig the things you say, but dear lord. That's a dork uniform right there. (You can wear this if you want to look like a child who got lost on the way to the school bus stop...and as you are a shorter fellow, I can't say I recommend it.)

No, I know it sounds weird, but he looks great. We are in Atlanta, you can die if you wear too many clothes! Husbunny is an Actuary though...
posted by Ruthless Bunny at 9:58 AM on May 2, 2013

Take a look-see at this ensemble. (The heather grey is more summery.).

You have manly styling, well-constructed and flattering pockets fore and aft, and you can dress it up or down based on shoes, belt, shirt. What you don't have are the dorky, droopy side pockets that make cargos so shlubby.

Please note the excellent choice of footwear, which is the element that makes or breaks dudes in shorts.

Yes, they are spendy, but buy once, wear often.

This seems to be the Year of Dudes Wearing Goofy Shorts (see the rest of the Nordies shorts selection), but I would gently steer you away from any of that. Wait till you're an Old Dude Who Gives Zero Fucks and Wears Shorts before you go with polka dots, marine mammal prints, and rolled-cuff pastels, please.
posted by nacho fries at 9:59 AM on May 2, 2013

The key to shorts is to avoid bagginess, which fortunately is less of a problem retail-wise than it has been in previous years. The issue with cargo shorts is that even well-fitting cargo shorts still have 1.5 trillion giant pockets which will all bag out and make you look like one of those guys who buys everything three sizes too large. Get something that fits well and as phunniemee says hits above the knee.

Also: Nthing Oxfords (but I would, wouldn't I?) and I'd say, TBH, pretty much eschew polos whatsoever if you're wearing shorts unless you're tennising it up. Polos are very hard to wear well.
posted by shakespeherian at 10:03 AM on May 2, 2013 [1 favorite]

Cargo shorts rarely look good. The lumpy pockets are unflattering, they are shapeless and no one over the age of 9 looks good in them. Get a pair of shorts that fit nicely, don't flare and follow the shape of your leg, the recommendation to aim for maximum butt flattering is right on target, there are shorts out there to make anyones butt look good. Think the fit of a jean but avoid jorts.

My very dorky husband has, with some gentle guidance moved into the realm of nice shorts that hit just above the knee, with a smart T with a print on and a light short sleeve button down shirt thrown on, open over the top to dress it up a little. This way he can still wear the dorky Think Geek tshirts he loves, or something with a graphic on, but it looks a little dressy and he can button or unbutton it to change the look up depending on where he is. He might not be a fashion plate in a magazine but it's a big step up for him.

Make sure your tshirts fit nicely, don't go baggy because you think it makes you look thinner it doesn't. Make sure your belly is covered ( if you have one) nothing is worse than a guys belly hanging out over the top of his shorts and not being covered by his tshirt.

There is a lot of disagreement as to what "style" is so you probably won't get a lot of agreement here, as it is more an art than a science. If you find you don't like fussing with your clothes too much creating uniform of something you like, like say my husbands tshirt, shirts shirt combo or whatever works for you, and then just mixing and matching with in that can remove some of the stress. Remember go for what flatters your body type and shape before trying to follow fashions, if the 2 coincide then great, but well fitting clothes that flatter are more attractive than being right on trend but in clothes that don't suit you.
posted by wwax at 10:18 AM on May 2, 2013

Best answer: right. ditch the cargos for all but the most casual occasions. Listen to phunniemee & shakes about length and fit.

Flat-front shorts that hit just above the knee and are made in nice fabrics will help. If you're doing cut-offs, do them almost knee length and with a cuff.

If you're going with a button down shirt, roll the sleeves, don't wear a short-sleeved one. If you do wear a short-sleeved one, make sure it in no way resembles a business shirt with short sleeves. Generally, this means a boxier cut, linen or printed fabrics. If you're going with a t-shirt: no slogans, heavier weight fabrics.

Shoes are tough. I, personally, don't like a man in sandals. I get that that's a personal preference, but there it is. Shoes are tough because socks look wrong with shorts. So you're stuck with shoes that look okay or are comfy without socks (or finding peds that stay up and don't show. good luck with that). Low slung Chucks and Chucks-like sneakers are okay. Topsiders, if you like them; slip on loafers work.
posted by crush-onastick at 10:19 AM on May 2, 2013 [6 favorites]

Dear god... Leave the cargo-ironing, twee characters, and short-sleeve oxfords to "Husbunny." An appropriate business casual look for a rabbit I'm sure, but definitely not "stylish."

Those J. Crew things are pretty much all looking nice and grown-up and...sleek? Sleek. Fit is important. Fully second "With tee-shirts, fit is important. It needs to be intentional."

Lands' End Canvas has put out some iffy stuff in the last couple of seasons but the shorts look okay except for the pleated...pleated camo? Like I said about iffiness. I dig the "Bandana Print Linen Shorts" and would wear them with a neatly fitted tee, possibly one with a subtle but neat print, like one I saw recently that was grey with a line drawing in darker grey, of an elephant, that went all around one side.

Classic summer fabrics like linen or seersucker in well-tailored, "clean," fairly close-fitting styles will not let you down, style-wise, and will adapt to a wide range of go-withs. You can wear a fairly formal short with fairly casual tops and footwear, and you can wear a fairly casual short with fairly formal ~ and ~ . If I was a dude and forced to wear cargos I would clean them up with penny loafers and a nice button-down shirt. If I had a very classic and conservative pair of seersuckers, I might bust out the concert tee and flip-flops. I feel that works with shorts in a way it doesn't always with pants; your legs may vary?

The thing about prep is that the cohort it boomed with is aging so it can now be a dated look; tread with caution -- if you have one preppy component, leave it at the one; don't top seersucker shorts with a loudly coloured polo.
posted by kmennie at 10:31 AM on May 2, 2013 [5 favorites]

Sorry dude, but no cargo shorts unless you're camping or hiking.

Just above the knee (knee cap should show), no pleats, no cargo pockets. Relatively fitted but not too snug. Belt. Shoes with no socks - loafers, boat shoes, moccasins.

posted by amaire at 10:43 AM on May 2, 2013

if you have one preppy component, leave it at the one

Solid advice.

I find the all-out preppie look intolerable, since it reeks of collegiate smugtard; but a tweaked version of it can be quite appealing.

I also retract my earlier short suggestion due to length. Agreed that we need to see some kneecap there.
posted by nacho fries at 10:59 AM on May 2, 2013

The biggest thing is how they hang on your body.

Complicating factor that may or may not apply: skinny legs. This can complicate things.

If you really want to up your style, you may have to be brave. Ditch the polos and loafers/boat shoes. Let the length fall at the knee or even lower. Plimsolls/lace up sneakers are good. But avoid running-type athletic shoes. Socks, if you want to keep stinkfoot at bay, but keep them low to no-show. Light boots/high tops can work pretty well.

Echoing others: Nix the pleats. Cargo shorts only if you have cargo. No baggy unless these are physical work clothes.
posted by 2N2222 at 11:06 AM on May 2, 2013

Phunniemee, crush-onastick, and kmennie have sounded all the appropriate warning bells about Things That Go Wrong When Dudes Wear Shorts.

Until you gain more confidence in your sense of style, stick to flat front, fitted-but-not-tight, just-a-tad-above-the-knee shorts in neutral colored cotton, linen, or seersucker. NO denim! NO extra pockets or loops! Never camo, and keep away from prints in general for the time being. Prints significantly up the difficulty level in terms of putting together the other elements of your outfit.

Sneakers should be canvas with low cut socks or no socks. Go for classic Vans, Converse (Jack Purcell or Chucks), Sperry boat shoes, and other summer sneakers of that ilk. Sandals should not, under any circumstances, have any velcro on them, and the fewer straps the better. If you could go whitewater rafting in the sandals, put them back on the shelf and walk away. I personally think leather loafers and moccasins are a little too "statement-y" for you right now. Stick with the sneakers and basic sandals.

If you wear a belt, make sure it's casual enough to go with shorts and sneakers. Brown leather that's well worn in or fabric webbing are good belt materials. Pay attention to the buckles too. They should be understated and not made of shiny metal unless they are the D-ring kind of buckle.

NO short-sleeve button down shirts. That's what all the guys I know wore in their late-teens and early-20's to look preppy-stylish. That was ten years ago. It's not a good look anymore. If you're cold and need to layer, go with a long-sleeve cotton henley, or a long-sleeve casual button down with the sleeves rolled up instead.
posted by keep it under cover at 11:17 AM on May 2, 2013 [1 favorite]

Whatever style of shorts you select please remember that if it's warm enough for shorts you do not need socks.
posted by mareli at 11:17 AM on May 2, 2013 [2 favorites]

Men's clothing really doesn't offer that much variety. Consequently, wholesale rules like no pleats, no short sleeve button downs, etc. really aren't that useful - it's all about tailoring and details like fabric.

That said - shorts are implicitly and terminally casual. If it's warm enough for most men to consider wearing shorts, I'm of the opinion you can pretty much wear whatever you want. If you were talking hot weather wedding and needed tailored poplin or linen or unlined open weave jackets, then you'd need to tread more carefully - but for this sort of thing all you really need to do to look more put together is closer fits, solid colors, and finer fabric.

In other words, all the same stuff men wear, in general - just a bit nicer or higher quality. It's really not that hard.
posted by NoRelationToLea at 11:34 AM on May 2, 2013

Some people like polo shirts. Personally, I haven't worn one since high school, when I wore them almost exclusively. (...and it was "Polo" brand polo shirts, from TJ Maxx and Marshalls, as I aspired to be anything other than the wretched dork I still am.)

Most men wearing polos look like schlubs who are trying to dress better than a t-shirt but still maintain that insouciant atmosphere. Instead, wear short-sleeved sport shirts - button downs. You can go to Sierra Trading Post and, on a good sale, get five or six of them for $100 - closeouts and last year's fashion, but who gives a shit. You can be as wild or mild as your personal style dictates.

For a slightly dressed-up look, shorts - even ratty cargo shorts - with a long-sleeved linen shirt or one of those Hemingway Cuban shirts.
posted by notsnot at 11:46 AM on May 2, 2013

I live in Phoenix, and my nerd of a (late 20s) male partner regularly wears Dickies shorts from high school with ratty Vans and gamer tee shirts. Everywhere. I would frankly consider myself a life success if he would stick to chucks and solid tees with the shorts - I've had minimal victory in this regard - but but the previous posters are working from somewhat higher standards, methinks.

OP, if you absolutely must wear the cargo shorts, and assuming they actually fit you and are not hanging off your ass (if they are, go ahead and burn them now) then I'd stick to solid color neutral tee shirts in a decent grown-up sort of material, neither skin tight nor super baggy, and ordinary sneakers like chucks, or non-sport sandals. You won't look stylish, but you'll be relatively inoffensive for casual hanging-around. Whatever you do, do NOT wear baggy cargos with a slogan tee shirt and an oversized short sleeve plaid button-up over top. EVER.

If you want to invent in a slightly more current look, everyone above has given great advice re. the lengths and styles you should be looking for; I happen to land staunchly in the anti-polo-shirt camp, thinking they make you look like a cellphone salesperson - and the short-sleeve button up is, as you can see from the previous disagreements, a pretty strong hit-or-miss. Personally, I theorize that if your shorts are simple (NOT CARGOS), you can probably get away with a casual button-up - just buy your own size and don't leave it hanging open (unless you are Fabio and/or on a beach vacation in the tropics). Basic tee shirts, though, are always ok for casual settings, long-sleeve button ups rolled up in lighter fabrics are classy if done decently, and everyone has pretty much covered the shoes issue (don't wear oversized skate shoes unless, like my boyfriend, you want to look like an overgrown middle-schooler though mmk?!)

If all else fails, find someone in person who has a reasonably decent style sense, and have them "check" you or approve/disprove your choices before purchasing/wearing.
posted by celtalitha at 11:56 AM on May 2, 2013

Seconding celtalitha's suggestion of having a friend go shopping with you. Either have a friend whose style you like shop with you or ask them to send you links of items they would buy/suggest for the upcoming season. My son has pretty good fashion sense and he's had a friend ask him to go on a shopping trip. He was fine with it. He took cell pics of the looks that 'worked' on the guy(with the cute salesgirl!), for the friend to reference later because he obviously didn't buy everything.

I have to say, I loathe every one of those Lands End shorts. They're all too short, and the prints are bad. Plain. Go for plain colors. Closer to knee length. Never pleats. NO flip flops on any guy over 12.
posted by toastedbeagle at 12:59 PM on May 2, 2013

NO flip flops on any guy over 12.

A nice (like, really nice) pair of sedate, brown leather flip flops can look totally nice and perfectly adult. Requires neatly-kept feet, though.
posted by phunniemee at 1:09 PM on May 2, 2013 [1 favorite]

Whatever style of shorts you select please remember that if it's warm enough for shorts you do not need socks.

This is not true. Some people's feet sweat too much to go sockless, and going sockless will wear out your shoes much faster. Not to mention they may start to stink.
posted by keep it under cover at 1:11 PM on May 2, 2013

get these 7" Stantons and roll 'em up once, or the 5" version and let them be.

Oh lord no, speaking as a (cough) mid-career coastal gay, the only men who roll their shorts are gays under 25 and most of them look silly anyhow.

Some people's feet sweat too much to go sockless, and going sockless will wear out your shoes much faster.

Not only that, socks are shock absorbers. If you're on your feet for any length of time, going sockless = more foot pain. This is why God made no-show socks. (Uniqlo makes them too--scroll down to "short"--and they are a godsend.)
posted by psoas at 1:29 PM on May 2, 2013

A great resource for tips about dressing like a damn grown-up (which I hate doing) is Put This On. And here are some things that they had to say about shorts. In case you don't feel like following the link:
- Get Gurkga shorts, or cut off & hem some pants.
- Acceptable colors = khaki, white, navy.
Though I myself deviate from this and bring black, gray, and green into the mix.
(And of course, there's always denim to consider.)
posted by D.Billy at 1:47 PM on May 2, 2013

My god, I had no idea that Men's Shorts could be so controversial. I encouraged my boyfriend to purchase two pairs of cargo shorts for camping last year (apparently an acceptable use for cargo shorts). He wears them around town when it gets hot out. I wonder if I've doomed him to sartorial hell??

My only advice would be to avoid prints. Unless you want to go all out and wear plaid shorts, a Hawaiian shirt, sandals with black socks, a Panama hat, and a huge camera around your neck. There's a time and a place for that, I guess.
posted by Elly Vortex at 2:30 PM on May 2, 2013

He wears them around town when it gets hot out. I wonder if I've doomed him to sartorial hell??

Here's the thing with cargo shorts: there's nothing inherently wrong with them. They get the job done, they're perfectly serviceable downstairs coverings, and no one's going to give a second look to a random dude strolling down the street wearing an ordinary pair of cargo shorts.

But no one's looking at random cargo short dude and saying, "now there, there's a guy with good taste."

If you're looking to buy new shorts, and specifically looking to up your game, style-wise, the advice to stay away from cargo shorts is spot on.
posted by phunniemee at 2:52 PM on May 2, 2013 [4 favorites]

I agree that you should never show any sock when you are wearing shorts, but of course your feet get sweaty and gross. That's why you need those no-show loafer socks that slip around the lower half of your foot.

And flip-flops are only for the beach. If your feet are hot, get some high-quality leather sandals that you slip into (there should be no flipping or flopping).
posted by theuninvitedguest at 3:11 PM on May 2, 2013 [1 favorite]

The issue is going to be length. Nothing off the shelf is going to be the right length for you so I suggest you buy something like what people have suggested and then get them hemmed up a bit so they end at the right point.
posted by srboisvert at 5:08 PM on May 2, 2013 [1 favorite]

Nobody mentioned Kuhl?
posted by overleaf at 10:05 PM on May 2, 2013

avoid prints

Yes to avoiding things that look like those baggy loud long swim trunks that used to be popular, but you can do prints.
posted by kmennie at 7:03 AM on May 3, 2013

This is pretty good advice though it is a bit patronizing. Shorts for men under 6 feet tall who are not rail skinny are a pretty restricted set.
posted by srboisvert at 7:57 AM on May 3, 2013

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