The rules for wearing shorts that every gentleman must follow

In decades past, the rule on shorts was simple: Gentlemen do not wear shorts, unless playing sport or on holiday. If I’d been asked to write this article a few years ago, it would have been a much shorter read, a simple repetition of the previous sentiment would have been as much as I could have penned on the subject. But as years have passed, style rules have relaxed. In the same vein as the relaxation of rules regarding ties in the work place or no brown in town, shorts have transcended their way through the confines of their sartorial stigma into the mainstream style stakes, and it’s not as unnerving as we all thought it might be.

Historically speaking, shorts were meant just for children, but like many style staples today, their place in current society harks back to their military association. In WWII shorts were introduced into military uniforms both for comfort in warmer climates, ease of movement when running and due to fabric rationing. These days however, they’re everywhere, from the well manicured lawns of the English countryside to the beach clubs of the Hamptons. But, like everything, there are a few rules to wearing them that you need to make sure you’re obeying this summer.

Not too short/not too long

The length of your shorts is as, if not more so, important as the fabric and colour choice you’re about to make. They should sit just above the knee. Too short and you’ll look like you’ve fallen out of a 80s fitness video, too long and you’ll look like your younger brother during his skater-boy phase in the 90s – which, let’s be honest, we’d all rather forget.


Not too baggy/not too loose

As a general rule of thumb, it’s better to be too close than loose. In order to avoid the chicken leg look you need to remember that shorts only add bulk to your upper leg, leaving the thinner lower leg open to ridicule and a baggy short will only further emphasise this.


Steer clear of cargo shorts

Cargo shorts may be practical, sure, but in my mind they are up there with the highest of cardinal sins against dressing. Therefore, unless you plan on trekking through the amazon or traversing the african bush anytime soon, they hold no place in your wardrobe. Opt instead for a khaki or camel short in a strong cotton or cotton-twill blend.


Don’t be afraid to look slightly preppy

Some of the best dressed men can been found on the streets of Bermuda (hence the Bermuda short). Due to soaring temperatures in summer, men have been sporting them for decades on this stylish island. The key to their success? The stylish pairings with preppy pastel coloured or embroidered shorts with block coloured linen shirts and beautifully fitted blazers in simple earth tones or navy.


Shoe choice is vital

Driving shoes, espadrilles, boat shoes or penny loafers should be your shoe of choice when it comes to pairing footwear with your shorts, anything else should be worn with severe caution. Also please note that socks should never be worn (or at least seen) when wearing shorts.


One final word: Unless you work in fashion or at one of those uber trendy start ups where there are slides instead of stairs, weekly ping pong matches and “break-out rooms” with astroturf on the floor instead of carpet, then when conducting business or attending a formal event, trousers should always be worn.

Main image: by Adam Fussell, styled by Holly Macnaghten. Featured image Pinterest



Holly Macnaghten is the Fashion Director at The Gentleman's Journal

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