How To Wear Shorts: 16 Outfits That Are Perfect For Summer 2022

Wearing shorts needn't be difficult. Here's how to get cut off right every time.

Words by: Charlie Thomas

Let’s keep this, well, brief: shorts are a summertime essential. Even if you prefer wearing trousers or jeans year round, there will be times when shorts are required. Whether you’re enduring an especially hot day in the city or you need a pair for your next vacation, shorts will keep you cool in a way trousers simply can’t.

But which style should you go for and how to wear shorts with poolside aplomb? From finding the right length to settling on the perfect design, here’s everything you need to know.

How long should shorts be?

Massimo Dutti

Getting the length right with shorts makes all the difference. Go too short and you risk looking like you’re 20 years late to P.E. class; go too long though and you’ll be entering the dreaded three-quarter length territory, which is usually only occupied by hikers and tourists.

For the perfect length you want to aim for something in between, with the hem finishing just above the knee. A flattering length for smart casual shorts such as chinos or tailored versions, this helps elongate the leg slightly without showing off too much flesh. That’s dress code-friendly for all manner of occasions from drinks in the pub garden to casual Friday in the office through July and August.

For shorts that are more athletic, or for styles that are functional like cargos or utility shorts, it’s possible to go slightly shorter. One or two inches above the knee gives these styles a more contemporary feel, which better suits weekend wear like hoodies, crew neck sweatshirts, tees, polo shirts and sneakers. But on the whole it’s worth staying safe and opting for the middle ground.

What materials are best for shorts?

Todd Snyder

Fabric can drastically change the look and feel of shorts, so it’s worth keeping this in mind when investing in your own. For sharper styles of tailored shorts, look out for materials typically associated with smarter clothing like chino cotton, cotton twill and linen blends.

Versatile and easy to style, these fabrics lend a smart casual flair to shorts, ensuring they’ll pair well with similarly adaptable pieces like Oxford shirts, knitted polos and chore jackets. They’re also incredibly breathable, especially linen, with its open, loose weave and lightweight fibres, which let air circulate around. Smart shorts don’t come more practical.

There are other materials worth thinking about though, especially when it comes to alternative short styles. For utility-style shorts, for example, performance fabrics are ideal and transform them into incredibly versatile, all-weather pieces. Coated nylon for example is a waterproof alternative to cotton, and while waterproof shorts might sound like an oxymoron, they come into their own when you go hiking with any valuable goods. Store a phone, wallet or camera in your pocket, and nylon will help to keep them dry.

Key shorts styles for men

When it comes to finding the right shorts for you, it’s important to consider the style, along with when and how you’re going to wear them. This will dictate what type you go for, from classic chino shorts to something more functional like cargos.

Chino shorts

Men's chino shorts worn with long sleeve polo shirt

Luca Faloni

For a classic pair that’s easy to style and works with a wide range of looks, chino shorts are the no-brainer that will find a home in every wardrobe. Simple in design and cut from the same fabric you’d find with your favourite pair of chinos, these are perfect for daily or weekend wear in summer and work with everything from Oxford shirts to polos and tees.

They usually come with a simple waistband with belt loops, flat-fronted thighs with slanted side pockets and two pockets on the rear. Easy-wearing colours include navy and stone or off white, which combine well with everything from tonal shades to other neutrals as well as earthy tones like green and brown. A warm-weather workhorse.

Tailored shorts

Suitsupply

For something a little smarter, tailored shorts are worth consideration. Just like a pair of tailored trousers cut off at the knees, tailored shorts are simple but effective. Often made from fabrics like cotton twill and linen blends, their minimal design makes them a blank canvas for pairing with similarly smart casual pieces like knitted polo shirts or crew necks.

The sharpest of all shorts styles, these are a natural pairing for summer-friendly leather shoes such as loafers to Derbies, but also combine well with minimal white sneakers and luxe sandals if you want to keep things laid back.

Cargo shorts

Todd Snyder

Cargo shorts are easy to get wrong. Just like their long-legged cousins, cargos can look bulky and ill thought out; in short, they can easily ruin your entire outfit. The trick is to go for a pair with a slimmer cut, and one with more minimal design details. Think simple pockets rather than traditional military ones and a tailored cut instead of a wider leg.

Cargos are a worthy choice for their practicality, which comfortably trumps that of regular flat-fronted shorts. The side pockets – the defining feature – makes them especially handy for day trips or travelling abroad, with buttons or zips helping secure essentials like passports, phones or headphones when on the move. They’re also the ideal style for workwear looks.

Drawstring shorts

Men's drawstring shorts worn with a tee

The Resort Co

For ultimate comfort, drawstring shorts are hard to beat. Expanding and contracting with you as you move and sit down, they are infinitely more comfortable than designs with a fixed waistband. They’ll feel like pyjama bottoms, but with fabrics more closely associated with smarter styles of trouser like chino cotton or linen blends, drawstring shorts have the potential to be a smart casual summer staple.

Wear them as you would a regular pair of chino or tailored shorts and combine them with button downs, Cuban collar shirts and tees and finish with retro running shoes.

Men’s Shorts Outfit Inspiration

Sportswear-inspired shorts

Men's retro drawstring shorts worn with a t-shirt, preppy cardigan and baseball cap outfit

Aime Leon Dore

A pair of sportswear-inspired drawstring shorts might be the summer garment you didn’t know you needed. With a slightly shorter length and an elasticated waist, this is a style you might have traditionally seen on the tennis or basketball court, albeit updated with a breathable cotton fabric and slanted side pockets.

Comfortable and easy to style, try wearing a pair with a printed T-shirt, retro sneakers and a cardigan.

Light blue shorts

Men's pale blue shorts outfit with a shirt and grey v-neck sweater

Suitsupply

While navy is an obvious choice for shorts, given they can basically be worn with any and every colour, light blue is a compelling substitute. With a slight nod to Riviera style and mid-century LA poolsides, pale blue is ideal for pleated chino or tailored shorts. It works with neutral tones like stone, beige and grey, which allow it to pop as a subtle statement.

Classic navy shorts

Men's smart casual shorts, shirt and loafers outfit

Ralph Lauren

If you buy just one pair of shorts, a navy tailored pair is your best bet. Simple in design and incredibly easy to wear, you can smarten them up for a sunny day in the office by combining them with a crisp blue shirt, brown leather belt and matching brown loafers. Or, alternatively, throw on a white T-shirt and sneakers for a clean, versatile summer look.

Off-white shorts

Men's linen shorts with black top and white sneakers outfit

Rag & Bone

White jeans and trousers are difficult to wear, mostly because the sometimes-harsh shade can dominate your entire look. Also: ketchup. With shorts though it’s far easier as they take up less real estate and allow other items to enter the mix, while simultaneously (hopefully) showing off your tan.

Try off-white shorts with a simple long sleeve crew neck in a darker shade like navy, and finish with clean white sneakers. Can’t miss.

Relaxed fit shorts

Men's grunge shorts outfit with check overshirt and canvas high top sneakers

AllSaints

A little known rule for wearing shorts: go wide. Slim-fit shorts can be restrictive and when they’re too tight, things get incredibly unflattering for the wearer. A relaxed cut is far more comfortable in the heat, and combines well with other laid-back pieces like oversized tees and boxy cut shirts.

Bring together all three for an easy going spring outfit, and finish with a pair of perfectly beaten canvas high tops.

Vintage sportswear

Men's white shorts, knitted polo shirt and sneakers summer outfit

Reiss

Take your cues from vintage sportswear and look to tennis stars of the mid century for your summer outfit inspiration. Incredibly stylish with a muted, neutral colour palette, there are plenty of looks to take interest in.

Start with a simple white short, knitted polo shirt and white sneaker combo, which wouldn’t have looked out of place on Wimbledon centre court in the 60s.

Keeping shorts simple

Men's green shorts, blue crew neck and suede sneakers summer outfit

Luca Faloni

For spring and summer looks, it’s often best to keep it simple. Pay attention to fit and complementary colours, and just enjoy the sun. Try a slim pair of green shorts with a navy crew neck and complete the fit with sand suede sneakers. You’ll look cool, calm and collected regardless of the occasion.

Navy and white

Men's navy shorts with white Cuban collar shirt and sneakers outfit

ISTO

For a classic summer combination, you can’t go wrong with navy and white. The two complement each other perfectly, and wear well regardless of the social situation. To try it yourself keep things minimal with a pair of navy chino shorts – sitting just above the knee – and a white Cuban collar shirt, which channels a subtle bit of Riviera style.

Cargo shorts

Men's slim cargo shorts, striped shirt and Harrington jacket outfit

Faconnable

Cargo shorts aren’t as difficult to wear as you might first think. Find a pair that’s slightly more minimal in design and less militaristic, and they can be worn in virtually the same way as any other chino or tailored shorts. That is with a tee and loafers, or – like above – with spring-ready items consisting of a striped shirt and windbreaker jacket.

Shorts with knitwear

Men's pleated shorts, shawl neck cardigan and espadrilles outfit

Brunello Cucinelli

Shorts work surprisingly well with knitwear, whether a tailored polo or something chunkier like a shawl collar cardigan. Try the latter and pair a navy take with a tonal T-shirt and relaxed fit, pleated shorts, for a smarter alternative to what is a timeless, naval-inspired colour combination.

Safari-inspired shorts

Men's safari inspired outfit with beige combat shorts, Henley top and safari jacket

Banana Republic

When it comes to creativity, warm-weather dressing doesn’t present a lot of options. However, one way to inject some personality is by turning to classic safari style, which is a surprisingly rife genre for inspiration. It starts with the colour palette of neutral, off-white shades, but the garments themselves are worth taking a closer look at.

Combat shorts are a classic safari staple, while a multi-pocket shirt and desert boots also have their place in the safari cannon. Keep the fits relaxed and finish with a red neckerchief, which adds a subtle pop of colour that keeps things from being too tonal.

Drawstring shorts

Men's green drawstring shorts, white short sleeve shirt and sneakers outfit

Alex Mill

Again, styling drawstring shorts is easy. Think of them as a traditional pair of chino shorts and pair them with other summer basics like polos, white tees and short sleeve Cuban collar shirts.

Opt for the latter in a relaxed fit, and complete the look with a blue neckerchief and matching blue canvas sneakers for an understated finish.

Co-ord shorts

Men's co-ord shorts and sweatshirt outfit with sneakers and baseball cap

Kith

For an alternative take on summer style, try a co-ord, or a matching top and bottom half set. This will keep getting dressed in the morning an incredibly simple exercise and means you can focus on the right accessories, such as baseball caps or complementary socks.

Going sockless with shorts

Men's shorts, crew neck sweater and leather bot shoes outfit

Boglioli

To inject a bit of Riviera cool into your look, try going sockless. While white sports socks undoubtedly look great with trainers, they jar with leather shoes, so get rid of them for a more refined take on summer dressing.

Leather boat shoes, for example, look their best sans socks, especially when combined with pleated shorts and a simple crew neck.

White linen shorts

Men's white linen shorts with a bright blue shirt and espadrilles outfit

Faconnable

Another way to try white shorts is by opting for a pair made from linen. The fabric has a matte finish that mutes the shade slightly, making it feel less harsh on the eye. The breathable nature of the fibre also ensures you stay cooler for longer.

White is a natural pairing for navy, but it also works well with light shades of green, pink and blue.

Cut off shorts

Men's cut off shorts with an Oxford shirt and blazer outfit

Todd Snyder

One interesting way to wear your shorts is by cutting them yourself. Whether you take some old chinos and cut the legs off, or trim down an existing pair of shorts, the unique fraying you’ll get will give your reborn style plenty of individuality which is often lacking with regular shorts.

Try yours with a denim shirt, which complements the ruggedness of the fraying, and finish with espadrilles if things really heat up. For a smarter take, throw an unstructured, summer weight blazer on top for an interesting alternative to a classic smart casual look.