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How to wear shorts

My absolute favourite outfit is a pair of shorts worn with a crew-neck jumper or an old sweatshirt. It reminds me of those evenings when you come in on a late flight from a holiday. It’s a look that always makes me smile when I see it on the catwalk. Thank you, Kim Jones at Louis Vuitton spring/summer 2014, look five. Fashion so often really is just about the simple pleasures.

My three-point holiday shorts plan goes like this: 1. The length can be shorter on holiday. 2. Channel Jude Law’s playboy self-confidence in the Talented Mr Ripley, mixed with Picasso, topless and smoking while working on a canvas in the south of France. 3. Ignore everything you’ve read about shorts trends of the season and wear what makes you feel good.

But this season shorts were a big trend on the catwalks, and there was a fairly broad church of ideas. Though if you were to pinpoint one key look, it’s probably a looser, longer Bermuda shape. This style is reflective of a general shift in men’s fashion towards a softer, more fluid silhouette. The Bermuda was seen at Alexander McQueen, Jil Sander and Balenciaga, which all offered tailored versions.

A shorts-sporting model at Louis Vuitton’s spring/summer 2014 menswear show in Paris. Photograph: Fairchils/Conde Nast/Corbis

Be warned: it’s a tricky look, especially if you’re not very tall, because there is a danger of your upper leg being swallowed in fabric and/or looking like you’ve got a skirt on. Not that there’s anything wrong with men in skirts, but that’s an entirely different discussion. If I were to road test the Bermuda look, I’d probably start with a pair by JW Anderson in denim. Longer, looser shorts resolve issues around too much thigh and too much leg hair. Witnessing a work colleague’s thigh fuzz isn’t everyone’s cup of tea. The Bermuda wins, being a friendlier length. And if you strip out the catwalk volume, you’re left with a knee-length, tailored short that can be filed under “useful”.

A more troubling idea the catwalk proposed is that one might want to wear shorts with a pair of socks yanked up. Now, I have a personal beef with this look because as a child I was made to wear brown velvet knickerbockers with white knee-high socks – a look frequently chosen for pageboys at 80s weddings. This style affectation, which cuts up your leg twice – once where the short falls and once where the socks finish – is best left to the models. Let’s face it: shorts just do look better without socks.

More shorts in the Jil Sander spring/summer 2014 menswear show in Milan. Photograph: Gabriel Bouys/AFP/Getty

No conversation about shorts is complete without talking about sportswear. For a lot of men their relationship with shorts begins and ends at the gym, and when it comes to exercise, it seems no shorts look is complete without a pair of Lycra leggings underneath. This style, favoured by cyclists or runners, also has catwalk form. See one of the most influential catwalks in menswear: Givenchy. This is one styling concept that certainly gets around the leg-hair dilemma.

Some final shorts thoughts: short suits are hard to pull off. Skater shoes are an easy on-trend footwear option with shorts. Prada and Dries Van Noten’s Bermuda alternative was a silky, boxer-style number – it’s worth a look. And no, combat shorts are not back. That’s all.

Simon Chilvers is men’s style director of matchesfashion.com

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