Welcome to shorts season – it’s been a long time coming.

People have strong opinions on shorts. There are those who wear them for as much of the year as possible, and then there are those who wrinkle their nose at the idea because they just don’t ‘do’ shorts.

If you’re in the latter camp, I suggest you reconsider. Shorts are a summer staple, yes, but they’re particularly relevant to the preppy ‘we summer in the Hamptons’ look that’s so appealing right now. There are chino shorts, there are denim shorts, there are breezy linen shorts-and-shirt sets, which feel like pyjamas but are legitimate daywear. This summer, shorts even have a presence in the workplace and as eveningwear.

Harrison Ford making the case for short shorts at the 1982 Cannes Film Festival Credit: Getty
Abraham: 'Casual shorts should have a slight worn-in ease about them,' like the pair Brooke Shields wears here in 1983 Credit: NBC Universal, Inc.

But it’s the perfect everyday pair that has the potential to become the summer answer to your favourite jeans. That’s assuming you have the patience to find it, because shopping for shorts can be as time-consuming and tedious as buying denim. Knowing what to look for is half the battle.

‘The simple short is not so simple,’ says Adam Brown, founder of the much-lauded menswear brand Orlebar Brown, which now offers regular shorts, as well as its tailored swimming trunks. ‘There are so many colour options to choose from.’

Consider this a foolproof guide to finding the right pair for you.

Length

This is the first thing to consider, for men and women. Personal stylist and body-shape expert Anna Berkeley advises standing in front of a full-length mirror with a bath sheet in front of your bare legs, then raising it up, inch by inch, to work out your short-length sweet spot. ‘There’ll usually be two spots on the leg above the knee – often shorter than people expect,’ she says. ‘Sometimes it’s easier to buy a longer pair, then roll the hem a couple of times, or have them altered.’

Brown agrees: ‘There is no universally flattering length for every man. But you’d be surprised how flattering a shorter length can be.’

On the other hand, a shape making a surprise return to the style spotlight is the Bermuda short, which falls to the knee. ‘I think they’ve been much maligned, but they look really good on most people,’ Berkeley says. ‘They can look amazing with a heel or a nice strappy sandal.’

A pair of Bermuda-cut shorts by Sandy Liang
Valentino Ready to Wear Spring/Summer 2024 Credit: Getty

Fabric

As with jeans, a great pair of everyday, casual shorts should have a slight worn-in ease about them. ‘Garment-dyed cotton with rich colours has a lived-in look – the kind of shorts that look like you’ve loved them for years,’ says Brown. Another effortless option? ‘Loose-fitting linen shorts, with a pleat and drawcord.’

With women’s shorts, curvier body types should consider a fabric with a degree of stretch, Berkeley says. ‘If you’re more angular, you can cope with a stiff linen or a non-stretch denim.’

Linen shorts by Marks & Spencer

Fit

For women, Berkeley recommends a flat front, with either a side or front zip. ‘Even an elasticated waistband can be rather good, as long as it sits flat once it’s on.’ If you’re bothered by the silhouette of the pocket bags in your shorts, as she’s found many of her clients are, she suggests cutting them out. Don’t let them get between you and a great pair.

For men’s shorts, the fit goal is ‘easy, tailored, draping off your body’, Brown says. And don’t dismiss a loose-fitting style: ‘Loose-fitting does not mean poor-fitting. Find a style that gives you more room to move, [which can inject] a little more drama into your look.’

Soeur
Asket

The bad news? There’s no escaping the trying-on session, and it is important to check that you can sit and walk comfortably in a pair of shorts before committing to them. ‘You don’t want them to cut off your circulation,’ says Berkeley. ‘Some people do squats in the fitting room, some people have a bit of a stretch – it is worth doing a few acrobatics.’

But if the advice here can help narrow the options, our work is done.

Try these for size...

Women’s shorts 

Organic cotton denim, £210, Issue Twelve; Cotton blend tailored, £165, ME+EM; Linen blend, £24.90, Uniqlo and Comptoir des Cotonniers

Organic cotton stripe, £150, By Malene Birger; Cotton belted, £79, Olive

Men’s shorts

Linen, £72, Everlane; Drawstring canvas, £100, A Day’s March

Organic cotton, £119, Oliver Spencer; Linen, £59.95, Massimo Dutti; Cotton-twill, £195, Orlebar Brown 

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