Not many men are confident in a pair of shorts. Not truly. Not in the cooler parts of the northern hemisphere anyway. And as a result, the menswear party line for the past decade or so has stubbornly been fixed when the weather is warm: stick on a pair of tailored shorts which hit just above the knee. End of conversation.
There’s no room for confusion and there’s no need to be ‘that’ guy in the shit shorts, vest and flip flops, with a patchwork of skin shades sprouting from the most unexpected places. Except that all that is now changing.
Such is the nature of menswear, just as you thought you were on solid ground in your tailored thigh-grazers, the rules are changing again. Yes, tailored shorts are still a solid option, but suddenly there’s a whole host of other attractive styles that play with length, texture and silhouette. Here are the eight pairs that offer a shortcut to sweat-free style this summer.
In the not so distant past, cargo shorts were the de facto king of summer leg-barers. Unfortunately, under their reign, the people suffered. Cargo shorts became the lazy man’s summer legwear of choice and most often came paired with an offensively bad (or just plain offensive) slogan T-shirt and some scruffy shoes that had seen far better days.
Now though, menswear historians are reappraising this proudly pocketed style. Gone are the unflattering hem lengths and faux worn-in finishes (which just looked like you’d stuck your shorts in the wrong wash cycle) and in their place come the cargo 2.0. The newer, younger model is slimmer and doesn’t have disproportionately large pockets.
Pair these with a breezy streetwear sensibility. Immaculately clean luxury sneakers will mark you out as card carrying member of club menswear, while an oversized T-shirt shape will demonstrate that you don’t shop for your tees by bulk. Think minimalism, to offset the technicality of the shorts. Think clean. Think Alexandre Mattiussi, not Top Gear on tour.
Retro Sports Shorts
Looking at pictures of tennis and footballing stars from decades gone by will elicit one of two emotions: abject horror or a hankering for the good old days. If you fall into the latter camp there’s good news. Getting your pins into a pair of retro shorts no longer requires patiently thumbing through the overstuffed rails of your local vintage store and hoping for the best.
That’s because designers have dug deep into the archives to bring back the best short styles from the days when sports kits went easy on fabric and heavy on exposed hamstrings. Think Bjorn Borg or Paul Gascoigne and look for retro details like side stripes, piped trims or curved hems.
That’s where the similarities with those two sporting legends should end, though. Rather than look like you’re in fancy dress, make like retro short fanatic Donald Glover and team a pair with an oversized T-shirt and old school skate shoes. Avoid wearing with shirts, flip flops and sweatbands like the plague, and you’re golden.
Unless you attended one of those schools with attendance fees equivalent to a Kardashian sponsored post, chances are pleated shorts will be relatively unfamiliar territory. What was once peak private schoolboy has become the short du jour for any self-respecting Pitti peacock though.
Like pleated trousers (also trending, FYI), the short version takes the basic premise of flat-fronted designs, but the small, preppy design twist helps you stand out on a beach. They don’t just look all debonair either: they’ll actually retain their shape better when you’re sitting too.
So, pleated shorts are the thinking man’s pick, but assuming you don’t want to look like a 1930s game hunter you’ll need to be wary about how formal the rest of your look is. Plump for a crew-neck T-shirt and some pared-back trainers or an open collar polo shirt and some chunky trainers to keep this old-school style feeling fresh.
Who loves short shorts? Menswear designers, that’s who. And after a couple of drinks, we’ll admit that we do too. Before you baulk at the prospect of exposing “underbum”, let us first clarify that there’s a difference between short shorts and hotpants. It pays to be precise. We’re talking about shorts that just hit the upper middle thigh, not anything that could be mistaken for your groin region.
Unsurprisingly, the condition of your legs makes a massive difference to how easily you can pull this fabric-swerving style off: slimmer or larger legs will have no place to hide, so short shorts are best avoided for those with bottom-half hang-ups.
Still, even professional sprinters will have to exercise some caution and avoid anything remotely snug. You’ll need to summon the spirit of Armie Hammer in Call Me By Your Name. For this you’ll need a loose long-sleeved Oxford shirt, worn-in retro sneakers and a pair of white sports socks. By covering up a around the ankle, you’ll be counterbalancing the acres of leg flesh on show.
Printed shorts are a funny old beast because there seems to be no mid-point on the taste continuum: they’re either solidly striped perfection or some crass comedy cartoon print. Too many examples of the latter have encouraged chronic aversion among most men, often at the cost of the former.
To wear the trend without your bottom causing eyes on stalks this summer, it’s advisable to stick to abstract camouflage or bold multi-coloured stripes which get the stamp of menswear approval. Too much? Look at micro print shorts for a quieter way to get involved.
The double-print co-ord thing may have taken sway on the catwalks, but at the pub or in the park, you’re going to want to curtail the crazy. For this a block colour open collar polo shirt or a classic white Oxford shirt is your best bet and let some black or tan penny loafers smarten things up a bit.
Outside of the gym and student halls, drawstring shorts should rarely be seen: or so traditional thinking goes. But with the rise of sportswear, drawstring styles have finally made a break from their natural habitat, which should be music to the ears of comfort-loving men everywhere.
The dangers of drawstring shorts are obvious: they have an unparalleled tendency to look like summer pyjamas. To avoid this, it pays to go for a darker colour, but if you do go light choose washed out pastel or off-white shades rather than grey.
Because of their already athletic status, don’t team drawstring shorts with logos or sports tops, not unless you’re actually going to the gym. Try a brightly coloured plain T-shirt or short sleeve shirt for your top half to ensure that you look like you’re put some thought into your outfit: white or grey options are just too basic.
For most people, denim shorts sit at the lazy end of summer dressing, and as a result most often look completely forgettable. This All-American fabric need not be a summer snooze fest though.
First and foremost is fit. Never go for anything form-fitting because short and tight sounds and looks precariously like a hotpant situation. Long and clingy, however, and you’re basically in pedal pushers: always make sure there’s comfortable room between your legs and the fabric of denim shorts.
Don’t go too obvious with the styling, either. Switching out a T-shirt for a Cuban collar shirt and you’ll avoid being mistaken for an overgrown schoolboy on his summer holidays.
Of course, you can go boring if you want to. Tailored shorts are undeniably failsafe and while they may not be the newest style, what they lack in originality, they more than make up for in versatility. If you can think of a summer staple, the likelihood is that tailored shorts will get along with it just fine.
Also, by employing a few canny styling twists here and there, these carefully cut classics have new tricks to offer. The easiest route to refresh tailored shorts is with all-over print on your top half. Working on the principle of balance, a Hawaiian shirt (or lightweight knit if it’s a little cooler) will let your outfit do the talking, while your trusty tailored shorts will smarten things up in the background.