The Complete Guide To Looking Good In Shorts

Despite what our sweat-drenched calves tell us in the summer, transitioning to shorts can be a risky move. Too short and paired with a matching preppy blazer over a shirt and tie and you risk looking like it’s your first day of primary school. Anything below the knee and you risk looking like a talent show reject in the year 2000.

There are a number of unwavering rules on how and when to pull out the knee-caps and with the world of fashion stylishly catching up with our need for a bit of ventilation, there’s a temptation to flash some leg before summer starts in earnest. Resist if you can. Spring weather is changeable and the azure skies you leave home under are likely to bruise by the time you’re off the bus.

We all know it’s easy to remove layers if you’ve overcommitted; less so to add ones you’ve not brought with you. “Don’t dive in too early,” says Phil Green, global senior operations manager for Farfetch, who advises leaving it until at least mid-May before breaking out your shorts under British skies. Also check ahead on your plans for the day – wearing shorts in spring is an acceptance that you’ve got no after-dark al fresco plans.

The Perfect Fit

Over the last decade, shorts have got shorter. It’s traditional to lay the blame at Daniel Craig’s overexposed legs, ever since his Ursula Andress-esque stride from the sea in Casino Royale, sporting a pair of La Perla shorts that took their name a little too literally. But what’s suitable for James Bond on a Caribbean beach doesn’t translate well to a barbecue in Colchester.

“A length that grazes the bottom of the thigh is best,” says stylist Dan May, who has worked with the likes of David Beckham and Eddie Redmayne. “It’s the most flattering to any body shape and avoids cutting off the knee.” May also advocates a cuff at the bottom: “It offers the illusion of shortness without showing too much flesh.”

That low-thigh sweet spot is imperative even if you’re trying to cover up rather than show off. As with your upper half, acres of fabric only serve to draw the eye to precisely the thing you’re trying to divert attention from.

Even men with big thighs should opt for a slight taper to the knee, while the edges of your shorts shouldn’t extend beyond hip width, otherwise you risk boxiness that makes your calves appear puny in comparison. Ditto anything with cargo pockets – having things to carry is a problem easily solved by picking up a bag.

The Right Shorts For Every Occasion

It’s easy to style a pair of slim, dark jeans in the winter months. But as we swap the snow for sun, those bottoms will start creeping above your mankles and over your knees, creating opportunities for all manner of fashion faux pas. These are the shorts to wear for every occasion, and how you should style them. Unless you’re a wildlife documentarian, mountain boots need not apply.

Chino Shorts

The fallback style for picnics, barbecues and balmy nights out on the Med, chinos let you swerve heatstroke while also meeting the bouncer’s standards if you’re out after dark. “Chino shorts are ideal because they can be dressed up or down if there’s a tighter door policy,” says Kasia Katner, lead stylist at online styling service, Thread, “the best cut being just an inch or two above the knee.”

Team your cotton chino shorts with a classic Breton shirt and a navy blazer and finish off with a pair of loafers. That exclusive rooftop party beckons.

How to wear chino shorts for men

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Tailored Shorts

If you’re confident that baring your calves won’t lead to a meeting with HR, this is the style to turn to Monday-to-Friday when the office temperature is set to ‘roast’. Try combining a pair with a neatly ironed shirt, expertly polished Derbies and a lightweight cotton or linen-blend blazer for a sophisticated look that would also work for a date or al fresco dining at an upmarket restaurant.

“Opt for minimal styles in pared-back, muted colours,” Katner advises, stressing the importance of a style that hits the sweet spot just above the knee. “It’s also best to avoid detailing like flap or zip pockets, and anything remotely sports-geared.”

How to wear tailored shorts for men

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Denim Shorts

As you start to spend more time in your pub’s beer garden than your own, it’s worth opting for a pair of hardwearing shorts that will withstand a few washes – because there will pint dribbles. And maybe even cigarette ash. Making knee-length denim options the way to go. Although not as breathable as their cotton and linen counterparts, denim shorts are durable and transition well to the evening. Better yet, a dark colour will hide most stains and combine well with a shirt come sundown.

Denim shorts have a knack for looking unkempt if styled incorrectly. So swerve the string vest and pair yours with care. Start with a simple slim-fitting tee, then layer a fine-gauge jumper or sweatshirt on top so your teeth don’t start chattering once the sun wanes.

Tread carefully, too. By which we mean it’s never okay to wear denim shorts with flip-flops. Running trainers can be tricky as well, so pull on a pair of canvas or leather low-tops and you’ll be in step with the rest of this low-key look.

The best ways to wear denim shorts for men

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Sports Shorts

Unless you’ve set up a sleeping bag somewhere between the leg press and the running machine, chances are you’ll wear your sweaty gym shorts outside the gym, too. Thanks to the era of athleisure though, it is lot easier to look fashionable as you do so. Opt for a subtle pair of sweat shorts (think logo-free jersey) in a versatile colour like black, grey or navy. Or lunge (not literally) towards a streetwear look with something heavily branded from the likes of Nike or Champion.

Keep the rest of your outfit on track by pulling on a crew neck T-shirt and bomber jacket or luxe hoodie. Similarly, neutral hues work well, but revving up the colour with one piece – either the tee or the jacket – can add some punch to this casual look.

How to wear sports shorts outside of the gym


Swim Shorts

Oddly – for a market that’s relatively small and seasonal – there’s an abundance of beach and poolside shorts choices for men. The simplest to wear are tailored styles in block colours and quick-drying fabrics that lend themselves to a post-dip lunch.

Cropped retro swimmers that are extra short in the leg have been in fashion for the last couple of years, but approach with caution and more than a couple of legs day sessions behind you. The same goes for bright, coruscating patterns. If you go bold below the waist, be sure everything above it is muted.

“Make sure whatever you do on top is simple, otherwise you can look a little try-hard,” says May. “Always make sure they’re dry and team with a polo shirt to make the transition effortless.”

The best ways to wear swim shorts outside of the pool


The Best Shorts Brands


Bridging the gap between high street and high end, this stylish British destination is known for timeless design-led fashion. The brand was a champion of the Cuban collar shirt, way before anyone else, and it has a fine range of shorts to go with this summer staple. While most other brands just offer shorts in cotton twill, Reiss has a line in linen, giving you more options for high-summer temperature fluctuations.

The Best Reiss Shorts For Men


Orlebar Brown

Sounds like a long lost Spanish conquistador, is actually the biggest name in luxury swimwear. These shorts are almost too nice to muddy in chlorinated waters, going through the same level of tailoring as suit trousers in a range of exotic prints you’ll want to hang on your wall. Recently, the British brand has also expanded to encompass the rest of your sartorial needs, including some dashing cotton shorts.

The Best Orlebar Brown Shorts For Men

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It’s no surprise that the world’s first choice for chinos does an extensive range of shorts. Ordered by the length of the in-seam, you can choose how much thigh you want on show, and there’s just as broad a spectrum of colours. Also look out for reliable, affordable, laid-back denim styles.

The Best Gap Shorts For Men

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Ralph Lauren

Ralph Lauren, along with Calvin Klein, resuscitated US fashion in the 1970s, with a range of preppy staples (knitwear, chinos, polos) evacuated from the campus library and onto the beaches of Cannes. Lauren describes his fashion as an American visualisation of Europe in the 1930s, so think what F. Scott Fitzgerald would strut around in if he was allowed to show a bit of knee and you’d be close to the mark.

Available in a range of fits (relaxed, classic fit, stretched slim) and bold colours and patterns, Ralph Lauren probably offers the best range of shorts off the high street.

The Best Ralph Lauren Shorts For Men

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The high-street monolith has a reputation for being able to pre-empt the latest catwalk looks without the need to rob a bank to refit out your wardrobe. When it comes to shorts they have one of the most varied selections out there. Alongside evergreen chino styles, this is a good place to come to try more niche trends without spending a fortune.

The Best Topman Shorts For Men

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Frescobol Carioca

Who is this Frescobol Carioca? Some sort of perma-tanned, fabulously flamboyant European designer who makes the finest tailored swim shorts somewhere on the Atlantic coast? Err no, it’s two British stockbrokers who, thanks to some sort of major DNA mix-up in the fashion lab, happen to make luxury beachwear that embodies the carnival spirit of Rio de Janeiro. Who cares where it came from, just appreciate the vivid mosaic patterns and tailored precision.

The Best Frescobol Carioca Shorts For Men

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While the shorts market can be a little overwhelmed by a-tad-too-beige options, don’t expect that from Gucci. Its ever-increasing popularity with social media-hungry millennials is precisely because its garments garner Instagram likes. As items of clothing, they always look better as a standalone statement so anchor with plain pieces that neutralise the extravagance.

The Best Gucci Shorts For Men

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Marks & Spencer

While the grand old duke of the British high street still does more than a few pairs of dad-friendly cargo shorts and even one or two three-quarter-length horrors, its huge range of shorts also includes some gems. Its tailored chino styles are some of the best value you’ll find anywhere.

The Best Marks & Spencer Shorts For Men

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Scotch & Soda

The favourite tipple of Ernest Hemingway, we’d like to think the legendary writer would extend his scotch and soda loving ways to the Dutch brand of the same name. Renowned for its progressive style, the label’s shorts offer a slightly more relaxed fit than the buttoned-up, more tailored names on this list, as well as hippy-ish designs that would suit an upmarket gap year.

A brand that flies under the radar, there’s little chance of being caught twinning with that guy from HR by the work photocopier.

The Best Scotch & Soda Shorts For Men

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The Sunspel philosophy is rather simple: make exceptional, everyday clothing from beautiful fabrics. As such, expect pure lightweight cotton shorts from the British heritage brand with a garment dye (rather than stitching together pre-dyed fabrics, the entire garment is soaked in colour). This softens the shorts and gives them a lived-in feel. Colour and pattern wise, this is not Gucci or Orlebar Brown, but for understated British gent abroad you can’t go far wrong with a Sunspel basic.

The Sunspel Shorts For Men

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Oliver Spencer

If ever there was such a thing as relaxed formalwear it exists in the mind of Oliver Spencer. The designer set up his eponymous brand a little over 15 years ago and it has risen to the top of the British menswear pile with quality tailoring, minus the stuffiness.

In terms of colour, pink hues reign, as do stripes. Short shorts are unwelcome, the Oliver Spencer cut is just above the knee, while linen and jersey are the favoured fabrics for a comfortable fit with zero pretence.

The Best Oliver Spencer Shorts For Men

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Ted Baker

Ted Baker is the king of surprise. Think you’re getting plain old chino shorts? Bam, there’s a paisley trim underneath to feast your eyes on. It’s the Ted way – a classic shape and fit hiding some marvellous peacocking finishing touch. The short range tends to be a playful take on the chino style, with a slimmer taper than preppy alternatives, while the colours range from playing it dangerously safe to rich and sumptuous.

The Best Ted Baker Shorts For Men

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Selected Homme

From the Danish clothing company Bestseller, which also houses Jack & Jones, Selected Homme differs from its stablemate’s vintage-inspired Americana with a minimal Scandinavian take on menswear. Readily available at Topman, ASOS and John Lewis amongst others, the brand’s printed shorts are minimal and tasteful while the majority of the range is block-coloured with a few striped pairs popping up.

You’ll get 100 per cent cotton at prices that leave plenty of change for a last-minute vacation.

The Best Scotch & Soda Shorts For Men

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Bonus: The Look Good In Shorts Workout

Shorts are, by their very nature, revealing. So make sure what you unveil is worth showing off. You don’t need Chris Hoy’s legs to look good in shorts, but some muscle definition will boost your confidence and enable you to dabble in more options. “Building a toned physique means you can be more experimental in your choice of shorts,” says May, “so that both tailored and sports-inspired looks work well.”

Two sessions a week is all it takes to build thighs worth showcasing. “You should train your lower body at least twice a week to really see progress,” says Luke Worthington, head trainer at luxury London gym chain Third Space. One session should focus on ‘knee-dominant exercises’; the other, ‘hip-dominant moves’.

Depending on your level, pick one exercise from each category, then perform in order – start with your big lift, then single leg, then your finisher. Try to complete four sets of each exercise – 6-8 reps on the heavy exercises, then 10-12 reps for single-leg moves and finishers.

Knee Session

Heavy: Barbell Squat

Stand with a barbell racked across your shoulders – pinch your shoulder blades back so the weight isn’t on your neck. Push your hips back and squat, keeping your weight on your heels. Pause, then drive back to standing.

Single Leg: Walking Lunge

Stand holding a pair of dumbbells. Step forward into a lunge with your right leg, sinking until your left knee almost touches the ground. Drive up straight into another lunge, this time with your left foot forward. That’s one rep. Repeat.

Finisher: Hack Squat

Stand with a barbell resting against your heels. Squat down to grab the bar, then drive up to standing through your heels – think of it as a deadlift with the bar behind your legs. Pause, then slowly lower.

Hip Session

Heavy: Barbell Deadlift

Stand behind a barbell, feet shoulder-width apart. Squat down to grab the bar, then drive up through your heels to standing. Pause, then slowly lower.

Single Leg: Barbell Step Up

Stand behind a box with a barbell racked across your shoulders. Step up with your right leg, then drive through your heel to bring your left leg to meet it. Pause, then step down, starting with your right leg. That’s one rep. After all your reps, swap legs.

Finisher: Glute Ham Raise

Think of this as a reverse sit-up. Lie face down in the glute ham raise station, heels under the back pad, thighs against the front. Bend forward so your head almost touches the floor, then drive yourself back up to the starting position.

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