There’s an old saying: the smallest dog barks the loudest. Wait, where are you going? We have a point. A beautiful woman doesn’t need to convince anybody she’s beautiful. A rich man doesn’t need to convince anybody he’s rich. And similarly, a well dressed man doesn’t need to convince anybody he’s well dressed by throwing on every trending piece from fashion week.
A look is only as good as its weakest link. Therefore, the coolest guy in the room is not always the one wearing a floral Cuban collar shirt or trousers so wide they could double up as bell tents, but the one that nailed the basics with an expertly fitted white T-shirt or sleek penny loafers.
These, and the other 13 classic pieces listed here, are the shortcuts to looking stylish while keeping shtum this summer.
Grey Tailored Trousers
Contrary to popular thought, tailored trousers aren’t just for sitting behind a desk in. A pair cut in a slim, tapered shape can just as easily serve as a step up from jeans on the weekend as a dependable choice for summer wedding separates.
“Tailored trousers are a menswear staple, and swapping to a lighter shade for summer months is a great way to update your wardrobe,” says Marks & Spencer head of menswear design James Doidge. “Going for a light grey tone pairs well with other neutrals or pastels for easy summer looks.”
Still think the only thing worthy of being at the end of your manly, calloused hands is a sturdy briefcase or sweaty gym bag? Firstly, get a manicure. Secondly, get a grip: chiefly of one of this season’s grown-up totes.
“Ease of use is this bag’s best feature,” says Jamie Cormack, co-founder of luggage brand Herschel Supply. “You can casually take it to the beach and then out to a nice dinner. It’s also a great piece to travel with – you can carry an extra layer for if it gets cold and have quick access to all your items.”
White Long-Sleeved Shirt
We’re firm believers that a man can’t own too many shirts, the most indispensable of the lot being a white long-sleeved version. No longer just the default uniform for bankers, lawyers and doctors, this classic piece still does the business.
“A solid choice no matter the season, a white long-sleeve shirt can take you from the office to a dinner out with absolute ease,” says the editor of menswear etailer The Idle Man, Tom Courcey. “For summer, you can always opt for a linen option for added breathability with a pair of light coloured chinos and loafers.”
Navy Tailored Shorts
The last thing you want when the mercury hits the high twenties is to have your legs trapped in an unforgiving furnace of a fabric. Stand up to the heat and leave a stylish impression with a pair of tailored shorts.
According to Henry Graham, co-founder of independent boutique Wolf & Badger, the trick is picking a classic colour commonly used on trousers. “Tailored blue shorts always look great on holiday and help you avoid looking like you’ve only met shorts for the first time that morning.”
If we weren’t already well versed in the Italian art of sprezzatura, we’d assume it translated loosely into something like ‘still looking good while it’s hot as balls outside’. The Mediterranean knack for blazing a trail in double digit heat comes down to light-as-air fabrics and fresh summer hues.
“A lightweight, deconstructed blazer is essential for staying smart in the warmer months,” says Doidge. “Fabrics such as cotton, seersucker and linen are great options – you’ll look smart, but not too formal. Style with a printed revere collar to nail any summer occasion.”
Without a pair of chinos in rotation, men would not only be less stylish during the warmer months, we’d probably be naked from the waist down. What other trouser gets us through the summer? Originally developed for the military before being adopted by civvies (including style icons such as Paul Newman), they’ve never gone out of fashion.
“With their classic preppy edge, beige chinos in particular work perfectly alongside a light blue Oxford shirt and a pair of trainers,” says Courcey. “For the summer, look for a pair cut in a slim shape that allows a little bit of air flow and aren’t too constricting.”
Yeah yeah, protect your eyes. UV rays, yada yada. The practical reasons for owning a decent pair of shades are obvious. But on a more superficial level, the right colour, cut and size can help bring symmetry to your face and hide crimes of excess, making them essential for summer.
“If a pair of sunglasses is uncomfortable, it’s because most are built in generic sizes for the impulse buyer,” says bespoke eyewear designer Tom Davies, who has made frames for the likes of Kevin Spacey and Heston Blumenthal. “Take time to understand your features and face shape and find out which style suits you best. This is unlikely to change so doing so pays off for life.”
No well-edited wardrobe is complete without the humble white T-shirt, ideally in supremely soft Supima or cotton-jersey. While a year-round essential that can also be used to add ballast in winter, its place on the menswear mantle is most important in summer when the light colour helps reflect heatwaves and therefore keeps you cool, in more than one way.
Doidge says the T-shirt’s greatest asset is its versatility. “There are so many styling options available. Wear one under a light coloured linen jacket for a relaxed take on summer tailoring; under an open short sleeve printed shirt for a breezy summer look; or on its own with blue jeans for a quintessential heroic men’s look.”
Breton Stripe Top
From sailors to Saint Lauren, few items have a history as varied or storied as the Breton stripe top. First worn by French mariners in Brittany during the 1850s (with a stripe for each of Napoleon’s victories), today the piece serves as a solid choice for underpinning smart-casual looks or wearing solo.
“Breton tops are one of my favourite looks,” says Graham. “They can be worn under a jacket in the evening, thrown on after getting out of the pool or just casually when out and about.”
The right pair of shoes will win you respect and endless compliments. A key part of the mid-century Ivy League look, penny loafers (named so because students would insert a coin into the front slit) are some of the most versatile around, and can easily bridge that tricky smart-casual dress code.
“They work with brightly coloured chinos, jeans and linen trousers,” says celebrity stylist Alex Longmore. “They are also practically the only shoe style that properly works with shorts. Make sure you break them in before wearing, as there is nothing worse than blisters and sore, swollen feet.”
Tailored Swim Shorts
Swim shorts are as synonymous with summer as ice cream or beer gardens. Perhaps this is because it’s always sunny somewhere and we’d probably, okay definitely, always rather be there. While retro, runner-style shorts have joined the (pool) party this season, models cut like chinos will always score a perfect 10.
“Tailored swim shorts are a summer essential,” says Longmore. “They can take you from beach to bar and slim fits do wonders for your physique. If tall, you can opt for a patterned pair; but as a general rule, a single plain colour is the best option. Navy, grey or bright red is a good choice – the latter being very Baywatch.”
Every well-dressed adult knows that the key to looking good for the long-haul is actually keeping your clothes on. A stylish belt saves any embarrassing slippages and can also be used to add a point of interest to an outfit.
“Waistbands are rising and shirts are being tucked in as men gain sight of their midsections once again,” says Time Out style editor Miriam Bouteba. “This calls for a belt that’s as much about form as it is function. A woven style is versatile and doesn’t look too heavy with chinos or trousers in the summer; it’s also a subtle nod to the ’70s trend that just won’t quit.”
Printed Short-Sleeved Shirt
As more and more men clock on to trends, it can be hard to stand out. Even Crazy Frank down the pub knows what a souvenir jacket is. A printed shirt in the style of Rami Malek or Harry Styles is the antidote. Use to add a little light-heartedness to a suit, or to make a solo statement alongside jeans or chinos.
“The look you want to go for is the modern day Hawaiian shirt, just slightly more fitted,” says Longmore. “Go for bright, bold colours and unique patterns, team this with simple separates and let the shirt do all the talking.”
Cotton Polo Shirt
Of all the ‘classics’ in the male wardrobe, the polo shirt arguably deserves the title more than any. A grand slam of design that has remained practically unchanged since the early 20th century, the sporting piece still refuses to look outdated when worn alongside anything from swim shorts to tailored trousers.
“Ever since Fred Perry and Lacoste emblazoned polo shirts, the world has been obsessed,” says Courcey. “This season, opt for a polo shirt in pink or blue and team it with a pair navy shorts and some white trainers.
Trends aren’t meant to last, right? That’s why we call them trends. So how long does a piece have to stick around before it’s considered a classic? Well, we’re calling it: the white sneaker has officially been inducted into the menswear hall of fame.
“I’m not sure we can credit the Scottish actor with this trend but ever since David Tenant’s turn in Doctor Who, wearing trainers with a suit has not only been acceptable but actively encouraged,” says Bouteba. “Pick up a simple pair of white sneakers and they’ll take you from desk to dancefloor and on to dodgy chicken shop if the night goes well.”