7 Men’s Fashion Trends That Shouldn’t Work (But Do)


The fashion industry can seem like the upshot of a bet between designers to see who can be most contrary. (How else are they going to get you to buy something new every six months?) Then there’s the 20-year trend-rehashing rule, which dictates that the statute of limitations on even the most grievous style crimes is at most two decades.

But for every menswear commandment that decrees you should or shouldn’t wear something in a certain way, or at all, there’s someone somewhere not just breaking but smashing it. Where there’s the most risk is where there also tends to be the most reward. Hence why these fashion trends should be all kinds of wrong – but can be oh so right.


Designers have come to a once-unlikely consensus that previously dowdy corduroy is cool.

“[This season], corduroy is paramount in the collections of many contemporary brands such as A.P.C., Cav Empt and Acne Studios, through bomber jackets, shirts and hats,” confirms Olie Arnold, style director at on-point e-tailer Mr Porter.

Before you have a wale of a time though, remember that those old geography teacher jokes are wheeled out for a reason. “Worn sloppily, corduroy can age you, so the trick is to make sure the cut and style are modern,” says Arnold. “Not 18th-century aristocrat.”

A jacket is the easiest way to get a good ribbing and not a mickey-taking, whether in a fail-safe neutral or a fresh colour: “My top pick for this season is [a] red or tan cord jacket, to spice up black jeans or chinos and a white slogan tee.”

How to wear corduroy in a cool way

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Boxy Tailoring

As square-shouldered tailoring was acceptable in the eighties, so it is now in the, er, teenies. “Oversized blazers and all things ‘anti-fit’ are all the rage this year,” insists Arnold.

The long and short is that boxy tailoring isn’t for everyone – at least not the short. “This is a much easier trend for taller chaps, as it can be rather unflattering otherwise,” says Arnold. “Worn incorrectly, it can make you look shapeless and clueless.”

Nor are the boxy blazers being proffered by the likes of Balenciaga, Maison Martin Margiela and Dries van Noten for everywhere. “I’d advise wearing them casually with a T-shirt and jeans,” says Arnold. “The aim with oversized tailoring is to achieve a laid-back, relaxed look. Officewear it’s not.”

Unless you work in mergers and acquisitions at Pierce & Pierce.

How to wear boxy blazers and loose tailoring

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Big, ‘Ugly’ Trainers

Granted, we can’t imagine stark white sneakers falling out of favour anytime soon, but with the nineties resurgent and minimalism receding, trainers that are more Jerry Seinfeld than Stan Smith are no longer off the menu.

“Raf Simons and Balenciaga are bucking the minimalism trend set by brands like Common Projects with chunky, outlandish designs in all manner of shapes and colours,” says Giles Farnham, head of the River Island Style Studio.

With big, ‘ugly’ trainers, the key is to let their ‘great personality’ shine. “Make your footwear the star of the show by keeping the rest of your outfit fairly pared-down,” advises Farnham, who also recommends styling freaky sneaks with cropped, tapered trousers: longer styles will gather, which can look awkward and distract from the shoes.

You’ll probably want your strides to be on the wider side as well, to counteract the clown-ness of your kicks. Especially if you have big feet.

How to wear big, ugly/chunky sneakers

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Short-Sleeved Shirts

Connotations of airline cabin crew meant that the short-sleeved shirt was given short shrift until recently. But by baring tattooed forearms, street style gods like Nick Wooster have weaned us off the cuff.

“Avoid veering into Google intern territory by going tieless,” counsels Farnham. “A short-sleeved shirt is at its best in a more casual ensemble. Try a Cuban collar design in a lightweight fabric and squarer fit, teamed with a crisp pair of chinos.”

Although the short-sleeved shirt is at home – or rather on holiday – worn open with sliders, you can upgrade it in formality. “Tuck it into a tailored pair of trousers teamed with penny loafers,” says Farnham.

Bear in mind though that function takes priority over fashion: “Never wear one in the winter, no matter how much you’ve been bulking.” Or how hot the destination of your flight.

How to wear a short-sleeved shirt in a stylish way

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Seventies Knitwear & Prints

Frankly, the whole seventies menswear revival could be filed under ‘trends that shouldn’t work’. Yet counterintuitive as it may seem, designers are turning the clock back as a recoil to modern minimalism, repurposing retro look-at-me pieces that are practically made for Instagram.

“Lush floral prints and globally-inspired graphics are all over this season’s collections on knitwear, shirts and tees,” says Mr Porter’s Arnold.

Harking back to the decade that style forgot until just now is not without risk. “To nail this trend without looking like you’re peacocking, team an overstated graphic or brightly coloured knit with simple, understated pieces such as a white shirt or tee and jeans or flat-front trousers,” says Arnold.

How to wear seventies knitwear and prints

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Double Denim

The ‘Texan tuxedo’. The ‘Canadian dinner suit’. The ‘Justin Timberlake at the 2001 American Music Awards’ (technically triple denim if you factor in the cowboy hat).

Despite these warnings from history, double denim can be a stroke of jean-ius. The set-in-stonewash rule is that the respective shades of your top and bottom halves should be different enough that it doesn’t look like you’re wearing a two-piece. For example, you might rock your body with dark blue jeans and a lighter jacket or shirt (not both).

Generally, it’s a good idea for your legwear to be darker, although there are exceptions, such as white jeans with a blue jacket. Speaking of which, mixing colours is an even more surefire way to avert uniformity: black or grey jeans with a blue jacket or shirt, say.

It’s also hard to go wrong with all-black-denim-everything.

How to wear double denim in a cool way

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White Socks

It used to be one of the incontrovertible style tenets: ‘No white socks except in the gym’. But then nothing is so certain to precipitate a trend as saying that it’s beyond the pale. Then there’s the fact that skateboarding and sportswear are white-hot right now.

“White socks are a big skate thing, so bring in a little skater attitude with cropped jeans or chinos in a relaxed or wide fit,” suggests Farnham. The ultimate expression is white socks with pool sliders, if you’ve got the confidence and a hot-enough washing cycle.

There’s a time and a place though – like the pool. “Never wear white socks in a formal situation, or with any kind of smart shoes,” warns Farnham. “It’ll look like you’ve forgotten your change of socks after a workout.” The time and place for that is at an Ivy League university in the fifties.

The best ways to wear white socks for men

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