The Best Men's Shorts Guide You'll Ever Read

Despite what our sweat-drenched calves tell us in the summer, transitioning to Men Shorts can be a risky move. Too Men Shorts 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 rejects in the year 2020.

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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 men shorts in spring is an acceptance that you’ve got no after-dark alfresco plans.

The Perfect Fit

Over the last decade, men 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 men 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 men 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 ankles 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.

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

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 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 colors,” 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.”

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 men 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 color will hide most stains and combine well with a shirt come sundown.

Denim men 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 men 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.

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 men shorts outside the gym, too. Thanks to the era of athleisure though, it is a 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 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.

Swim Shorts

Oddly – for a market that’s relatively small and seasonal – there’s an abundance of beach and poolside men 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 men shorts 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.

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“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 Shorts Brands

Reiss

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 men shorts in cotton twill, Reiss has a line in linen, giving you more options for high-summer temperature fluctuations.

Orlebar brown

Sounds like a long lost Spanish conquistador, is actually the biggest name in luxury swimwear. These men 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 men shorts.

Gap

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.

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 men shorts off the high street.

Topman

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.

Frescobol Carioca

Who is this Frescobol Carioca? Some sort of perma-tanned, fabulously flamboyant European designer who makes the finest tailored swim men 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.

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Gucci

While the men 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 precise 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.

Marks & Spencer

While the grand old duke of the British high street still does more than a few pairs of dad-friendly cargo men 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.

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.

Sunspel

The Sunspel philosophy is rather simple: make exceptional, everyday clothing from beautiful fabrics. As such, expect pure lightweight cotton men 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.

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 pretences.

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 men shorts-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.

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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 men shorts are minimal and tasteful while the majority of the range is block-coloured with a few striped pairs popping up.

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 men 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 men 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 a 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.

What Makes A Good Pair Of Shorts

Just like any well-made suit or dress shirt, shorts also have their own grading system to looking sharp, albeit a bit more casual. The three main criteria are simple: fit, material, length and patterns. Nail these and you’ll have one of the best looking summer outfits whether you shirt it or not.

Length

Below knee, above knee and men shorts. These are the three main length categories of shorts for men these days (unless you’re into reggae you shouldn’t be rocking three-quarter shorts). Choose lengths according to the rest of your outfit. Tees and singlets go with men shorts whilst below the knee and above knee shorts pair well with casual dress shirts and polos.

Fit

Would you wear a pair of shoes that don’t fit? The same answer applies to your men shorts. Whilst casual trends champion the idea that if a pair of men shorts are baggy and comfortable then they’re perfect, there’s more to it than that. For styling purposes, a baggy pair of cargos from 2003 just won’t cut it. What you need is decent tapering along the leg length which makes the wearer appear taller. There are rules though and that’s not to go too tight otherwise you’re in the hot pants territory. The public need not see the contour of your frank and beans. Fitment around your waist should also be comfortable without being tight. If you can wedge your index finger between the waistband and your waist, you’re on a winner.

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Material

Cotton, polyester, denim…men shorts come in a plethora of material variations so choosing the right one is essential depending on the occasion. Cotton is usually the go-to item for more smart-casual looks whilst polyester covers the athleisure segment and denim the casual/street style. There are also linen men shorts these days and these are perfect for the days where the mercury is proper high.

Prints & Patterns

The rules are simple for prints and patterns – make sure there’s the contrast between your top and bottom. Whether that be through colour blocking or contrasting patterns is entirely up to you. Just be wary of vertical lines as it can accentuate unflattering body lines if you don’t have the physique of Thor.