A Man’s Guide to Wearing Shorts

by Antonio on May 30, 2012 · 224 comments

in Dress & Grooming, Style

Few items in a man’s wardrobe seem to elicit as much debate as shorts do. Today we’ll uncover just why that is, and then offer some guidelines on the how, what, where, and why of wearing them. Guidelines I’m sure will be much debated! Let’s get right to it.

Why are some men reluctant to wear shorts?

Why is there so much confusion about such a simple garment?

In the late 19th and early 20th centuries there were a number of English words for shortened men’s pants. “Knickerbockers” were baggy pants that gathered below the knee, covering it. Shorter, tighter-fitting trousers that ended at the knee were “knee pants.” “Short pants” sometimes meant knee-pants and sometimes meant shorter garments still.

All of these varieties were clothing for boys, both unofficially and as part of many school uniforms.

Grown men didn’t start wearing shorts outside of extremely hot climates until after World War II, during which soldiers stationed in the tropics had been issued short trousers both for comfort and to ration cloth.

In the post-war years, shorts caught on as a specific uniform for some kinds of sports and recreation. They weren’t fashion items or clothing that could be worn outside of a specific athletic activity — much the same way that a biker’s spandex shorts and jersey wouldn’t be worn off the bike path today. Tennis players might wear shorts on the court, but would clean up and change into trousers before socializing afterward.

In the middle of the 20th century, shorts were considered athletic-wear only. “Shorts” was more likely to refer to a man’s boxer shorts, which he wore under his pants.

Shorts as a piece of comfortable, casual summer wear for men did not show up until the 1950s. Even then — championed by trendsetters in Hollywood and other men in the spotlight — the idea took a long time to catch on as “normal.”   There are still plenty of men alive today who remember shorts being basically clothing for young boys.

Shorts are a modern addition to a man’s wardrobe and thus are still finding acceptance.  Although common everywhere in North America, they are not common wear in many other parts of the world (to include hot climate countries).   

Interestingly, while shorter trousers have gradually become acceptable in most arenas, athletic shorts went through a major shift from short, boxer-style shorts to longer mesh shorts in the 1980s. These days it’s unusual to see the extremely short athletic shorts that end as soon as the hip turns into the thigh, though some runners do still wear them. For team sports, mid-thigh or longer has become the rule.

So shorts, at the end of the day, still have a boyish association. That’s no longer a cultural expectation, and no one’s going to think you’ve lost your mind if you wear them. Clothing manufacturers love the idea of being able to sell men even more pieces of clothing each season, and men love the cool comfort shorts provide, so that genie is unlikely to ever go back into the bottle. But it is still something we, particularly if you’re an older man, instinctively think of as “boyish,” even when we’re not conscious of making that judgment.

When to Wear Shorts

Shorts are a casual piece of menswear. So when to wear them?

The simple answer is two-pronged:

1. When there’s a good reason to (temperature, environment, location) and

2. When you’re not conducting business or attending a formal ceremony/event

Recreation with family and friends is always a good default category for “shorts times.” Beaches, private parties, outdoor sports and recreation, and anything else purely for fun and not in the company of strangers or business associates is definitely in the clear.

Even those situations, of course, need appropriate weather: wearing shorts when it’s cold out is going to draw attention. Wear them when it’s hot enough that you really want them, and switch to light trousers as soon as it’s bearable.

In our modern world it also seems worth saying that a man who plans on leaving an air-conditioned house to get in an air-conditioned car and drive to an air-conditioned building can endure wearing trousers no matter what the weather is like. At the point where you have that much climate control you might as well wear the sharper-looking garment that better compliments your build.

FYI – The only people that can violate these rules are Californians.  Please see Seinfeld.

Target practice in Australia is a perfect occasion to wear shorts.

When to Skip the Shorts

Business dealings of any kind call for trousers. Even if it’s just an informal game of golf, wear a pair of light trousers instead of shorts, regardless of whether other men are wearing shorts or not. Take a cue from the pros here (the exception being John Daly).

Any sort of structured event outside the immediate family and close friends is also a time to avoid shorts. Even casual luncheons, picnics, weddings, or other outdoor, summery sorts of events should merit light trousers if you’ll be meeting strangers or relatively unfamiliar acquaintances.

Never wear shorts anywhere a jacket or blazer is expected. If the situation calls for that level of formality, it also calls for more formality than shorts offer. A few cultures have exceptions to this (shorts with blazers and ties are acceptable business wear in Bermuda, for example), but in most of the world it looks both out of place and a bit confused.

Finally, be aware of wearing shorts when traveling the world.  In many countries it clearly marks you as a tourist and may draw unwanted attention.

How to Wear Shorts Well

As a lesser-worn piece of menswear, shorts prompt all kinds of questions: How long should they be? How baggy? How many pockets? Belt or no belt? And so on.

How Long Should Shorts Be?

The far left pair are too short in my opinion. What do you think?

Short enough that your knees are visible or just slightly covered if standing still. Long enough that you’re not showing the world you rarely tan your thighs; if I have to be specific, I would go more than 2-3 inches above the knee, depending on your proportions. Barron from the Effortless Gent backs me up here.

Anything past the knees has ceased to be “shorts.” Those are high-cut pants, which is something else entirely (and not very flattering).

Shorts that do come up to mid-thigh should be limited to lightweight athletic shorts, and should only be worn in athletic settings. Running shorts get more leeway than casual shorts because the expectation is that you’re not going to walk into a store or restaurant wearing them. Exercise devotees should bear this in mind, and should go home and change (and shower) before inflicting themselves on the public outside of gyms, courts, or bike paths.

How Loose Should Shorts Be?

To some extent this is a matter of taste and style. Worth keeping in mind, however, is that shorts add bulk to the upper part of your legs only. Your lower legs will be bare, meaning that everything above them will look thicker by comparison. The baggier your shorts are, the thicker the look. So baggy shorts make your butt and thighs look big — not a look most men are seeking.

A close fit in the seat and straight legs down to the top of the knees looks good on most men. The style is reminiscent of military shorts, and their descendents, the Bermuda shorts, which are good classic styles that people have had a generation or two to get used to by now.

A baggier fit is sometimes common on the golf course, where it evokes the knickerbockers previously favored in the sport. These should obviously always be belted, preferably with a canvas and leather belt.

Pockets, Patterns, and Styles in Shorts

“Cargo shorts” or safari shorts with side, front, and back pockets are great for hiking or working outside anywhere that’s hot but not particularly overgrown (or otherwise hazardous to bare legs). Outside of that, they don’t have much of a role in your wardrobe.   Let me be clear here: baggy, multi-pocketed shorts don’t look great in social settings.  These are ultra-casual and should not be worn to college social events.

Solid colors such as tan, khaki, white, navy, olive, and off-white are the most traditional styles for men’s shorts. Plaids, especially plaids with a white base, are a preppy look staple, but should be paired with at least a polo shirt to avoid looking like a frat boy (and no collar pop, please). Madras pushes the prep look even further, and should be worn with caution.

Notice how color affects the mood of the same pair of shorts. By introducing a brighter color you can take shorts from boring to eye-catching.

Louder-patterned shorts, the kind that look like Hawaiian shirts for your lower half, should be saved for beach vacations and Jimmy Buffet concerts. (Interestingly, these are often referred to as “Bermuda shorts,” presumably because of the tropical association, but true Bermuda shorts are civilian versions of traditional military uniforms from the Pacific islands and are almost always khaki or white cotton).

What to Wear with Shorts

Can You Wear Socks with Shorts?

Can you? Yes. Should you? Only sometimes.

Socks and sandals is an appropriate pairing for old German men on vacation and no one else. So if you’re wearing sandals, which is what you’d expect when it’s hot enough to need shorts, skip the socks.  And sandals are the most casual option: fine for beachwear, not OK for a graduation party.

Shorts worn with closed-toed shoes usually look best with ankle socks. Mid-calves are starting to cover almost as much skin as just wearing trousers would have, and if you’re going to be that covered you might as well look better in trousers. Knee socks and shorts are downright laughable.

Slip-on casual shoes like boaters or loafers are also good companions to shorts, and don’t require socks (though if you need them for comfort inside the shoe, most good shoe stores will have “ballet” or “invisible” socks that don’t show above the shoe).

Shirts that Go with Shorts

Shorts are casual, so the shirt should be too. Don’t wear a long-sleeved, button-fronted, collared shirt with shorts. Even with the sleeves rolled up it’s too much of a stylistic mix-and-match.

Collared short-sleeve shirts are usually the best choice for men who want to look good but stay cool and casual. These can range from button-fronted (seersucker is particularly nice) to your basic monochrome polo shirt. Hawaiian shirts, like loud-print shorts, should be reserved for occasions where a little obnoxious tackiness is part of the fun — tiki bars yes, regular bars no, even near a beach.

T-shirts and shorts is a look that flatters no one. It may be appropriate in casual settings, but it’s not going to make you look as good as other options.

Blazers or Jackets and Shorts

This is a very fashion-forward pairing. In a few parts of the world, most notably Bermuda and South Africa, shorts with business shirts and blazers is actually an established style, and tailors will happily make you a “suit” with short pants instead of trousers. Outside of those countries, however, it’s very much a “fashion-forward” look.

If you’re looking for more fashion-forward ways to wear shorts, visit Josh and Travis here.

Materials for Shorts

Before closing, it’s worth noting a few of the cloth choices men have for shorts. These are garments meant for the most extreme heats of the year, so there’s little point in wearing them if they’re not made from something lightweight and breathable. Unfortunately, the most comfortable fabrics are often more expensive to produce, so a lot of mass-marketed shorts will be made with a thick cotton that’s worse than wearing full trousers of a lighter, more breathable material.

Cotton Shorts

Cotton is a great menswear material for heat — if it’s woven right. It’s lightweight and breathable and is by far the easiest to wash and dry without special care. However, tight weaves of cotton hold hot air close to the body, and sweat or water evaporates from it very slowly.

  • Seersucker is one of the lightest cotton weaves, with a dimpled surface that lets air flow. It’s a joy to wear in the summer and one of the best options available.
  • Madras (true Madras cloth, not just the reddish plaid print) has a very loose weave that lets air flow and dries quickly. There’s very little domestic production in the United States, so it can be costly unless you happen to be in India.
  • Gauze is more commonly associated with medical bandages, but the large weave with its visible square gaps was used for tropical military uniforms for some time and is reappearing in consumer clothes as well. It’s another good option, though not as durable as Madras or seersucker.
  • Drill or twill are both tighter weaves that hold in more air and moisture. Unfortunately, they’re also cheap and common, and make up the majority of most commercial lines. Wear them when you need a bit more durability but aren’t expecting to exert yourself too much.

Linen Shorts

Linen trousers are more common than linen shorts, but if you can find a pair they’re very lightweight and comfortable. Linen tends to wrinkle more than cotton, but the distinctive creases are part of the style, like the bumps in seersucker. Don’t bother trying to smooth them out.

Wool Shorts 

Tropical-weight wools are used for summer trousers because of wool’s smooth drape, but that property is largely wasted in shorts. There’s not a real reason to buy wool shorts, even ones made from very nice, lightweight wool.


Athletic shorts are usually made of synthetics like nylon or spandex. For the most part this is beneficial — the loose weave of basketball shorts keeps the artificial fibers from holding in heat and sweat, while newer synthetics can actually wick moisture away from the skin and let air flow even better than a cotton weave.

Want more?  Then click on the image below to see Primer’s visual guide to wearing shorts!

Also – don’t forget AOM’s guide to dressing in hot weather.

In Conclusion

Watch the video to have me talk you through the article.

Shorts are a modern classic piece of menswear with a storied history. They have a place in every man’s wardrobe.  Just make sure you wear them right!


Written By

Antonio Centeno
Founder of Real Men Real Style
Author of the Internet’s Largest Style Video Library

{ 224 comments… read them below or add one }

201 Bruce June 6, 2013 at 7:01 am

Also BTW why do you guys in the states always wear t-shirts under your shirts, even on hot days? (according to what I see on TV). I remember watching NCIS and here’s Gibbs wearing a t-shirt under his long sleave thick-looking shirt, AND a jacket, in the office! Boy, he would have been sweltering! Meanwhile there’s Ziva standing next to him in a thin strapped little number…go figure!

202 Kevin June 6, 2013 at 8:40 pm

I’m always wearing shorts cuz they’re comfy, and in the winter with a hoodie. I like wearing shorts to places where most others don’t, the looks and comments you get sometimes are pretty sweet. I wear shorts to go hang with a group of friends at a bar each week, they all wear jeans.

203 Bob June 10, 2013 at 3:06 pm

I’m with Bruce on this one. I’m in the states, but I don’t follow that fad.
Regarding shorts, up until recently, I was not opposed to wearing below-the-knee shorts, like cargo type shorts, but now, I’m seeing way too much ‘Saggy-Baggy Long-Dong’ shorts …what a turn-off!

I generally don’t follow all the latest trends. Now, it’s the Plaid, Saggy-Baggy look. I can remember wearing Plaids when I was a kid. At that time, I was thought of as being out of fashion and I was called a goofy nerd. Now, Plaid is in fashion. How’d that happen?

So, in the light of practicality, I prefer just regular mid-thigh shorts – they’re just plain functional. Altho, everybody thinks that it’s ‘Gay’ – it isn’t. A lot of today’s clothing styles lack intellect – just plain S**ty!

204 Ken June 10, 2013 at 3:36 pm

Interesting article. However you did not mention how those baggy shorts make men’s legs look like toothpicks from the knee down.

205 Brett W June 14, 2013 at 7:50 pm

I’m relatively new to this site but this is one of the only articles I disagree with. I think shorter shorts is a good look in my opinion, but that’s likely because I dress quite preppy. Shorter shorts are becoming increasingly popular in fraternities and on college campuses, especially in the south. Also becoming popular is pairing shorts with a button-down shirt and the occasional blazer every once in a while.

206 Jenny June 21, 2013 at 1:46 pm

FINALLY. A good article about how to wear shorts. I know the boys may not like it, but as a woman, I have to concur with pretty much everything in this post :) Not that it means anything, but just my two cents.

207 Palifox June 29, 2013 at 3:25 pm

The shorts on the left are about right. The ones in the middle, OK, but the ones on the right are clumsy “Bombay Bloomers” as once issued to British Army in India.

In the style known as “Territory Formal” shorts of the shorter length would be worn with knee socks, closed shoes, white or pale blue long sleeve shirt and a tie, no jacket of course. Through the 60s and 70s. . Temperatures of course would be in the 90s and 100s F and air con was rare. Shorts with a polo shirt and sandal was acceptable casual wear in most situations.

208 Robb July 20, 2013 at 4:50 pm


That’s a pretty good picture of John Wayne on the way to the beach. He’s wearing espadrilles and carrying a bag that’s probably got sunscreen and a towel and a copy of Bridget Jones in it. He’s also wearing swimming trunks.

In other words,The Duke wore shorts when he went swimming.

209 M July 23, 2013 at 3:07 pm

Bruce…. The reason you wear an t-shirt/undershirt under your dress shirt is so that you dont get sweat stains showing. I’ve never understood why people thing its cool to walk around with sweaty shirts sticking to their body. And if you dont like full t-shirts, you can wear the an athletic shirt that has the armpits cut out so you can release body heat without sweating.

210 Andy July 30, 2013 at 2:17 am

As a man living on a Mediterranean island where the average summer temperature from the beginning of June till the end of September is 30 degrees, soaring easily up to 35-40 in July and August, my smarter shorts are always just above the knee and my sports shorts, which I wear daily, are several inches above the knee – the shorter the better. In fact, all I wear inside the house are very short shorts and flip flops – it is too hot to function otherwise.

211 Jim August 2, 2013 at 2:46 am

I live in Northern California and wear shorts year round. I like shorts that are about 3 inches above the knee. Anything lower just does not feel like shorts to me,more like half pants. Guys who wear shorts look sexy!

212 Peej70 August 10, 2013 at 3:11 am

I always love to wear shorts in the summer. I’m fairly chunky, and, I find something very sexy about wearing small shorts. They made my legs look attractively big at the top and slim at the bottom. I get plenty of curious looks and giggles from young people, but some women have wolf-whistled and find it all very sexy. My bum does feel fat in those shorts, although I love the whole feeling this gives; and no, I’m not gay, I’m blessed with a fat bum and “big skinny legs” – if you’ve got it, flaunt it..

213 Desert Rat September 18, 2013 at 5:08 am

Black t-shirt and Dickie’s shorts. Preferably khaki. A good look no matter what.

214 B September 24, 2013 at 10:16 pm

A serious question:

What if you simply don’t care what others think about your appearance?

I don’t mean to say that I’m dressing in torn-up, stained, and disgusting clothing, but rather: most of this advice seems geared toward the person who seeks constant approval from others, even those they don’t know (read: the opposite sex and business superiors).

In my case: I’m married, have no real concern for trying to attract other women anymore due to the first clause in this sentence, and have a job that has no dress code or expectation of fancy dress (I work at home). With that being said, I enjoy T-shirts and longer cargo shorts. Why is that a problem?

215 Nick September 27, 2013 at 1:35 pm

I agree with B. I honestly don’t care what is in for “fashion.” What should matter is style. If wearing khaki cargo shorts and a comfortable t-shirt is your style outside of a business/formal setting, then by all means go for it!

Cargo shorts and athletic shorts are the only shorts I own. I like to wear them more than jeans, though I do like the way I look in jeans. They’re just more comfortable for me than jeans are.

This isn’t to say I don’t know how to dress up. I clean up quite nicely when I throw on my suit or just a business casual (solid button up, tie, black slacks).

I just like to wear comfortable clothing. There is nothing wrong with that.

216 Ryan September 28, 2013 at 10:09 pm

The more I learn about traditional men’s fashion and the attitudes involved, the more obvious it becomes that it developed in cooler climes. Everything from the disdain for shorts and open-toed shoes to the insistence on jackets (and if you want to go whole-hog, undershirts as well) at all times, screams “clothes designed to keep you WARM.” I’m not so foolish to think that exposing skin is the best way to keep cool when the sun’s beating down, but until linen returns as a primary staple fabric (in the heat, even thin cotton is sweltering in comparison) and becomes readily and inexpensively available, shedding the layers and letting the breeze work its magic on more of your body is the best available option for most of us. Do what you will yourself, of course, but to insist that others suffer in excessively warm clothing purely for your own aesthetic enjoyment is to indulge in pointless selfishness.

In addition, I take exception to those in the comments who claim that dressing down indicates or leads to poor behavior. I personally spend nearly every day dressed down (t-shirt, jeans, and steel-toed boots for work; t-shirt, cargo pants/cargo shorts, and sneakers/sandals otherwise), and make an effort to be respectful and courteous wherever I am. There are good people and jerks among every class and group of people, and all you’re doing is letting confirmation bias color your viewpoint. No doubt my own confirmation bias plays a role, but some of the rudest and most self-centered people I’ve ever encountered were wearing very nice suits and clearly felt their social/economic position gave them broad license to act however they pleased.

217 Dirk G November 25, 2013 at 8:02 am

During the winter all I wear is a sweatshirt and shorts even if its like freezing. I like the comfy feeling of shorts and the cold air on my legs. If its kinda boyish to be wearing shorts, well I’m only 19. It think it shows manliness to wear shorts because you got to be comfortable wearing them in public and show your legs.

218 Addison November 27, 2013 at 2:41 pm

If your shorts are more than a 9″ inseam, you’re doing it wrong. You look like you can’t decide if you want them to be pants or shorts. They should never cover your knee. Ever. I am 6’0 and I usually wear 6″ inseam shorts.

~Don’t wear pleated shorts.
~Don’t wear cargo shorts.
~Don’t wear tennis shoes with non-athletic shorts.
~Always wear a belt.
~If your shorts are plaid then you must wear a shirt that is solid colored.
~If your shirt is plaid then you must wear solid colored shorts.

219 TroyJMorris January 2, 2014 at 7:30 pm

The article you link to for short length features models wearing long-sleeved collared shirts with shorts.

Every. Single. Image.


220 Jim January 20, 2014 at 1:04 am

All these shorts are far to long, shorts are meant to be SHORT, not short pants.

221 Brent Griggs February 10, 2014 at 4:00 pm

I just moved to a mountain community where even on the coldest day you always see some guy wearing shorts, even in the snow. It’s real laid back here, and guys wear shorts to go just about any place around here. Most of the teen boys here wear jeans to go out, hang out, smoke cigs, whatever.

222 Greg March 20, 2014 at 8:56 pm

I have big legs, so I wear my shorts just below the knee. I have tried everything, but they just get harder, not smaller. I even wear my kilt a little lower than standard because of my “tree trunks”, as my trainer calls them.
For those guys who say, “I don’t care about my appearance. I’m married.” Your wife cares. I’m a counselor. Keep yourself up. She’ll return the favor. Respect her and yourself, she’ll respect you.

223 End Wage Slavery March 23, 2014 at 2:56 pm

I’m not an old man, just a younger man with taste. And I must say that shorts on a grown man look ridiculous. As in it makes me think “This guy should be wearing a beanie with a propeller on it and going to his 8-year-old friend T.J.’s house to play Matchbox cars.” (This is why you don’t see them outside of the U.S., i.e. places where men still have taste.)

224 Mr. Steal-Yo-Girl April 6, 2014 at 8:25 pm

I want to change to cargo khaki shorts and polo and button up short sleeved shirts and was wondering if i could wear a white leather/canvas belt with nice Gucci gold buckle and how to wear it with them.

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