25 Best Shorts For Men

Tom Ford famously said that a man should never wear shorts. But, as men’s wear continues to contradict itself (think the return of old, bespoke tailoring and the rise in sports-inspired casual wear), we are equally seeing a return of the casual fashion bottoms made notorious by Nineties dads and mullet-rife trailer parks.

Click through the slideshow for the best 25 shorts for men in 2016.

A Short History

The short has had a love-hate relationship with men. The modern short silhouette came along in the mid-century, when the British military were looking for a way for soldiers to keep cool in warm places like Bermuda. It freed men from hot trousers in the summer months, providing less restrictive, more comfortable bottoms.

Hollywood style icons Paul Newman and Robert Redford picked them up in the Sixties and common men soon followed, before the Seventies saw shorts peak on the tennis court with John McEnroe. The aerobics-era of the Eighties saw shorts climax before the ‘normcore’ Nineties created shapeless denim and three-quarter length cargos, letting the dad dressers relish in the fact they never had to wear trousers again.

Ten years later, designers are reworking short silhouettes and prints into styles much like the ones seen decades ago. It’s a lot easier for men to buy stylish shorts these days, so click through the slideshow of the 25 best shorts for men, to get things started.

Breaking It Down

shorts for men

Despite their simple nature, shorts can still go very wrong. No longer one-type-suits-all, shorts come in a slew of styles, in differing lengths and various fabrics, making them occasion-appropriate for certain functions where a little relaxation is in order. From beach holidays to weekend getaways, summer garden parties to lounging around the home, the short needs just as much attention and planning as one would give their suit. Taking out the difficulties, we’ve compiled a complete guide on shorts.

When To Wear Them

shorts for men

Shorts are a casual piece of menswear – no arguments. You wear them because of the heat in summer, for comfort and as break from the restraints of trousers. Plus, they are offer a playful look to an otherwise ‘standard’ outfit. The big rule regarding shorts: they must not be worn in a corporate setting or in a formal environment (think weddings, funerals, formals and black tie).

The Big Five Types

Generally speaking, there are five types of shorts for men to take note of in 2016: dressy, casual, denim, swim and sportsluxe.


Shorts for men

A slight oxymoron, dressy shorts are practically cut-off trousers or chinos. The structured fit and finish of the pant remains, with standard pocket detailing, belt loops and a zip fly. Like trousers, the dress shorts will come in plain, neutral or pastel designs, which can be paired with almost everything tailored in your wardrobe.

In keeping with the formal vibe, opt for a button shirt in crisp, white and add a pair of summer loafers or brogues – always sockless. Tuck the shirt in for a more formal look and add a belt to blend in with the leather from the shoes. Feeling super suave? Add a blazer in a lighter hue so that it feels summery.


Shorts for men

The casual short will differ in look and/or structure from the dressier variety. The structure of the casual short is softer and can be buttoned up, zipped or tied with drawstring. A key component is the print. This season is seeing a trend graphic patterns in geometric shapes, camo and wallpaper florals, so take your pick.

Because these are very much statement shorts, match the bottoms with a muted white shirt – cut-off at the sleeves or a polo shirt or tee. Keep the shirt untucked in a shorter length or tuck it in (no belt) so the pattern below remains the features.


Shorts for men

The denim short sees a return to denim’s industrial American roots. With a focus on indigo, the jean short for 2016 is a great off-duty look. It represents an organic, earthy approach to casual bottoms, matched with the easy-go versatility of what regular jeans bring to a contemporary street wear look.

Some denim varieties are literally cropped jeans, still featuring the workwear functionalities of five-pocket details, brass zips and buttons. Then there are the new generation of indigo-hued shorts, using minimal details in washes that feel Japanese-inspired. Both are made to be relaxed, so don’t over think your outfit.

Swim Shorts

Shorts for men

The most playful of the shorts styles, swimwear comes in floral and animated animal prints this season, as well as hyper, block-colours. Not meant to be taken too seriously, these shorts are snap-button closed for a tight, retro vibe or cord-pulled for looser varieties, which provide a bit of roomier bunching.

Never wear them wet when away from the beach and pair swim shorts with flip-flops (thongs) and a tee or tank. Or nothing at all, making sure you stick close to water to avoid looking like a show-off.


Shorts for men

With the athleisure trend continuing its furore, the intermixing between sports and luxury fashion has not escaped the short. The silhouette of these shorts are evidently roomier, less structured and sometimes unhemmed and drop-crotch. The muted colour of the sports short gives it a parred down feel, not designed to draw attention, but more aligned with comfort and minimalism.

Going for a pair of gym-look, lounge-y shorts under a tee and sneakers is a great wind-down look for the weekend and post-workout, with the active-fashion hybrids designed for an effortless transition from sweating to street.

Rules of Length

Shorts for men

As a general rule, shorts should be short enough so the knees are visible, but long enough that you’re not flashing a horrid tan line from last summer. Shorts that do come up to mid-thigh should be limited to athletic body types, confident of having the pins to pull them off. This excludes swim shorts and retro-inspired casual pairs, which need a little shorter length to give-off those Seventies-vintage vibes. Final rule: never go past the knee (ever).

Baggier silhouettes should be kept to certain versions of swim shorts and sportsluxe types, which get their urban, lounge-y attitude from appearing a touch oversized. Dressier shorts, like the Bermuda, are a classic style that need a close fit the leg and crotch (the seat) and follow tapered down toward the knee.

Fabric: In Short

Shorts for men

Cotton is the most common short fabric. It’s lightweight, breathable and comfortable – all things expected of summer clothing. Common cotton types this season are seersucker (a light cotton weave with a dimpled surface); twill (a durable, denser cotton); and linen (wrinkly and breathable).

Other key fabrics for shorts in 2016 are denim and chambray for casual shorts, and neoprene, jersey and polyester for sportsluxe types.

 Click through the slideshow for the best 25 shorts for men in 2016.

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