A Man's Guide To Wearing Shorts


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.

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.

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?

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.

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