Oh how we all scoffed at talk of a nineties revival in menswear. Big, flashy branding? No chance. Oversized tailoring? Not on this side of Don Draper. Bumbags? Bumbags, mate?

A few years later, of course, all of these things have come to pass, refreshed by fashion’s spin cycle just like eighties styles (acid wash jeans, pinstripes, pastel colours) were before them. Today, puffer jackets and tracksuits may be the toast of menswear, but just a few years ago, it was unthinkable.

All of which raises the ugly question of what might be around the corner for men’s wardrobes. Do you remember the turn of the 21st century? Do you remember what was trending, who the trendsetters were?

We do, and what we recall is the faux hawk, beads worn without irony, deep-V T-shirts and Justin Timberlake in matching double denim with Britney Spears. Less Y2K, more why 2K, why?

If menswear really is about to get the Millennium bug, these are the trends that could be making a comeback, ranked from the most likely to the please-god-no.

Baggy Trousers

Likelihood: 100%

The skinny fit’s stranglehold on menswear (and, by extension, your genitals) came later in the noughties. At the turn of the century, loose-fit trousers gave a man freedom. Perhaps a bit too much, in fact. Formal or casual, styles billowed shapelessly and puddled around the ankles. No-one seemed to care. This was a time before you could Instagram your sneakers.

But if you think slouchy styles are a thing of the past, then you haven’t been paying attention. Relaxed trousers are already back. Skate styles, generous tailoring and loose-fit denim are calling time on ubiquitous slim fits, with Mark Ronson and designer Patrick Grant two of the most prominent wide receivers.

If you want to follow suit, follow the new rules: stick to tailored silhouettes and straight- (not wide-) leg cuts, with hems finishing at the ankles, not two inches under your heel.

V-Neck T-Shirts

Likelihood: 80%

In the noughties, Welsh rugby player Gavin Henson and assorted other perma-tanned frat boys paved the way for today’s muscle-fit horror show by stuffing their cuboid physiques into slim, deep-V T-shirts that sliced through their bulbous he-vage like cheese wire through Wensleydale.

Never forget. But never again? Don’t count on it. While we’d agree that the chance of a navel-kissing V-neck is vanishingly slim, that doesn’t mean V-neck tees are gone for good. Nor should they be.

V-neck sweaters have already made an unlikely comeback in this season’s knitwear. And if you do flick the V as a tee, keep them in neutral shades of grey, white, navy and black; always in casual outfits; never let the V point lower than two inches below your collarbone; and if you look like Tom Selleck without a top on, do us all a favour and consider some manscaping first.

Stuffy Suits

Likelihood: 69%

Before Mad Men came along to nip and tuck our tailoring game, every man’s two-piece looked like a politician’s suit. Boxy around the shoulders, too roomy in the chest, with the hem of the jacket creeping halfway down your thigh. There’s a good chance it had three buttons, not two.

The big trend in tailoring in recent years has, in many ways, been the opposite of that. Casual styles in an array of fits, textures and colours have loosened the way men think about formalwear. We even wear trainers with suits now.

But fashion likes nothing more than reacting to the norms of the day, which might explain some of the silhouettes we’ve seen from Balenciaga, Tiger of Sweden and others in recent seasons. If you don’t want to go that far with it, look for wider lapels and roomier legs at the more directional end of the high street, in places like Topman.

N*Sync Hair

Likelihood: 60%

We have no market data to back this up, but we firmly believe that firm-hold, wet-look gel was a pillar of the global economy around the early noughties. Men’s hair at the time came spiked like a Medieval mace weapon. And if it wasn’t spiked, it was slicked back, or fringes were pushed up like freeze-frame tidal waves.

Boybands from N*Sync to Green Day all pushed statement hairstyles to the masses, with more than a few opting for highlights or primary colour dyes to boot.

It’ll take a lot for the pompadour to flop out of favour right now, but men are starting to experiment with riskier styles again. Undercuts and curtains have both made unlikely comebacks, and earlier this year Zayn Malik dyed his hair green in what could be a sign of things to come. Are you ready to frost your tips?

Trucker Hats

Likelihood: 51%

Ashton Kutcher’s grinning Millennium mug should have made it impossible for trucker hats ever to come back from the dead, but we’re seeing portents that this demonic style will rise again.

Baseball caps in general have been a firm fixture in menswear in recent seasons, pairing not just with sportswear but smarter takes on streetwear and workwear, too. Alongside that is the resurgence of outdoorsy style and now, brands like Patagonia are offering their take on the mesh cap style.

But what about the garish ringleader of this naughtiest of noughties trends, US brand Von Dutch? Perhaps you think its fluoro designs are too, well, bloody awful, to ever be rehabilitated. We’d remind you once again that minimalist menswear is giving way to big patterns and seventies opulence. Sorry, but it’s only a matter of time.

The Going-Out Shirt

Likelihood: 44%

In the early days of the 21st century, there were twice as many nightclubs in the UK as there is today. For a young man with 30 quid in his pocket and a twinkle in his eye, Saturday night was something to dress up for, and the Going-Out Shirt was a statement of intent. Usually ill-intent, but never mind.

Metallic shades, contrast collars and prints so loud they’d make Peter Stringfellow feel sheepish were all fair game, usually worn with a pair of bootcut jeans, some pointy shoes and maybe, just maybe, a Maori necklace.

We’d like to think this trend will never boomerang back into existence, but the signs are there. Muted prints are moving over to make way for statement patterns in men’s shirts, and even silk is part of the big seventies revival in menswear. Whether they come with a two-for-one deal on Smirnoff Ice, we’ll have to wait and see.


Likelihood: 36%

A new century should have been a time for hope and renewal, but look back at the moody emo kids of the time and you’d think there was population-wide joy deficiency.

This look was all about wearing your angst on your deliberately slashed sleeves. Combining elements of punk, grunge and skatewear, but mostly in black, the studded belts and long, straightened fringes screamed at an uncaring world, “I have feelings, okay?”

Well, the kids of 2018 have plenty of reasons to feel angsty, so maybe this trend is due a rerun. Skate brands have already found favour with streetwear scenesters. Hoodies and band T-shirts are back again. And to be fair, monochrome is never a bad shout. Let’s just hope the eyeliner stays on hiatus, along with My Chemical Romance.

White Vests

Likelihood: 25%

Any garment that attracts a nickname like ‘wife-beater’ should be viewed with forensic suspicion. This didn’t happen around the Millennium, with the likes of Eminem, Fred Durst and Craig David all wearing them regularly on stage.

For all their thermoregulation merits, however, white vests are never going to escape Jim Royle and trailer park connotations.

In recent years, no less than David Beckham has been spotted in one, showing off his tattoo sleeves in a rare sartorial misstep. If you’re going to copy Becks, look to premium loungewear pieces made from soft cotton-jersey. Under a dressing gown is about the only acceptable way to style this one.

Backpacker Chic

Likelihood: 19%

Perhaps spurred on by Leonardo DiCaprio in The Beach, young people around 2000 took gap years from work or education to find themselves (or at least some cheap mojitos) on some far-flung tropical paradise.

But as well as spiritual enlightenment and the odd STI, these crusty travellers brought back malaria-grade menswear from their time abroad. Even worse, they kept wearing it.

Flowing linen cargo pants, chunky wooden necklaces and man-of-the-world tattoos were some of the worst offences, but don’t forget bandanas, ‘utility sandals’ and dreadlocks on people who shouldn’t have dreadlocks. At best it was scruffy. At worst, it was cultural appropriation dressed up as worldliness. Pass us the sick bag.

The Trilby

Likelihood: 2%

Surely not. Surely not. The 15-year-old crimes of Ne-Yo are not yet ready to be dug up and forgiven. Not now. Not on our watch.