The Best 90s Fashion Trends For Men (And The Ones You Should Wear)

Whether you look back on the 1990s fondly or cringe at their mere mention, there’s no denying the decade fostered some iconic looks. Grunge was good. The sportswear too. That said, it also played host to some truly awful trends – from boyband haircuts to baggy, well, everything. So with ‘90s fashion still in the spotlight, we’re looking back at the good, the bad and the ugly.

Below is our pick of the biggest ‘90s fashion trends. Some have proven their staying power while others have fallen by the wayside. From centre partings to bum bags, these are the ‘90s looks to know, and the reasons why you should (or, quite possibly, shouldn’t) welcome them back into your life.

Baggy Jeans

They swallowed shoes, they trailed on the floor and they absorbed rainwater like big denim sponges. Yet, despite their shortcomings, baggy jeans were everywhere in the 1990s. It was this way for most of the decade, until eventually the leg openings got so wide and the back pockets got so low that some young hip-hop artists were swallowed whole, never to be seen again.

In the years that followed, skinny jeans began to take over. Today, baggy jeans are making inroads into men’s wardrobes again, becoming a key denim trend. Granted, they’re not quite as severe as they were back in the day, but they’re not slim by any stretch of the imagination. To get the balance right, we believe a classic relaxed-fit jean is the way to go – the perfect way to keep this ‘90s staple alive without going full Limp Bizkit.


The Jacket Maker Allaric Alley Black Leather Biker Jacket

The 1990s isn’t the decade most associated with the leather jacket. That mantel would have to go three decades earlier, to the 1950s. This was when the popular image of the leather-clad, denim-wearing bad boy first began to crop up, with the likes of James Dean and Marlon Brando embodying a new era of disaffected youth.

But fast forward back to our era in question and a new batch of young male talent began to turn to the leather jacket once again. Stars like Brad Pitt, Johnny Depp, Jeff Goldblum and Matt Leblanc often wore leather jackets, ranging from oversized blazers to bombers as well as classic bikers.

The trouble was, unlike their ’50s forebears, the ‘90s take on leather was often rather ill-fitting, and unless you had the face of a movie icon you were unlikely to be able to pull it off. So today when considering the ‘90s leather look for yourself, consider fit above all else. Combine a flatteringly slim biker with pale wash jeans, a white tee and Converse and you’ll be on the right track.

Long Hair

For the last decade, short and mid-length cuts have reigned supreme, but there was a time when longer styles were the haircuts du jour. Nineties icons like Kurt Cobain, Brad Pitt, Johnny Depp and Leonardo DiCaprio made long flowing hair for men look good, while the mullets and Flock of Seagulls weirdness of the previous decade faded (thankfully) into obscurity.

Today, longer trims are very much back on the barbershop menu. Short and mid-length styles still rule the roost, usually accompanied by some sort of fade, but A-list style icons like Jason Momoa to Jared Leto are proving that long hair can still work three decades later.

Bucket Hats

We could sit and debate the pros and cons of bucket hats all day, but not unlike Liam Gallagher himself, you either love them or hate them. Either way, they’re bigger now that they were at Knebworth in 1996.

A staple of the ‘90s rave scene as well as Britpop, these simple brimmed hats have become a symbol of hedonism, securing their place as festival uniform along the way. You don’t have to buy one, you don’t even have to like them, but you do have to admit that the bucket hat has earned its place in menswear history.

High-Top Sneakers

Thanks to Air Jordan and Reebok, the ‘90s were filled with sky-high sneakers. Ankle-hugging basketball and aerobic footwear was ubiquitous and everyone, from kids to celebrities, was in on the action.

Usually, when a trend takes hold with such gusto, it fades pretty quickly, but high-top sneakers are bigger now than  they were in the ‘90s. These are sneaks with staying power and many of the styles that were popular back then are every bit as relevant today.


Windbreakers have been around since the 1970s, but they were particularly rampant in the ‘90s. Adorned with colourful prints and day-glo patterns, they were the decade’s casual outerwear of choice. Geography field trips? Check. Bank holiday days out? Check. Pub? Check.

For us, the windbreaker still holds relevance today, although we’d be inclined to stay away from the headache-inducing colourways. Instead, stick to classic two-tone designs and keep this ‘90s icon alive the right way.

Frosted Tips

Nineties boy bands have a lot to answer for. Beyond terrible music, frosted tips might just be their worst offence. For the uninitiated, this quintessentially ‘90s hairdo involved bleaching only the very tips of the hair, which was usually cut short and spiked up vertically with wet-look gel.

Should you consider bringing it back? Absolutely not.

Bum Bags

Back in the ’90s, when wallets were the size of bricks and we also had Game Boys, Walkmen and Tamagotchi to carry around, people needed some on-hip storage for their various accessories. That storage was the bum bag, aka the fanny pack. The ridiculous names were bad enough, but these hideous micro-bags also came in lurid neon colours and drew attention to everybody’s groins.

Surely they wouldn’t make a comeback? Well, yes and no. Reimagined as the cross-body bag, in tasteful designs and colours, the bum bag cleaned up like a rockstar in rehab. Louis Vuitton are now among the luxury brands selling them hard.


Is there any image more ‘90s than Fresh Prince-era Will Smith shrugging jovially at the camera in a billowing batik-print shirt, dungarees hanging jauntily off one shoulder? If there is, we haven’t seen it. These denim overalls were a staple of ‘90s wardrobes and although not every man had the cajones to pull them off, when they worked, they really worked.

These days, dungarees are primarily reserved for edgier dressers. While we can’t see them making a full-scale comeback, hats off to anyone with the styling chops required to get it right.

Popper Pants

Those of us who were there at the time remember the strange but not unpleasant breeze that crept in at the sides of these highly impractical track pants. We’re still not sure what the design was actually for. Instead of an outseam, these shiny joggers had a strip of poppers running all the way up to the upper thigh. An all-too-inviting target for bullies and pranksters.

They’re back but only the most hardcore ’90s revivalists need apply.


Not every style championed by ‘90s boy bands was destined for the cultural scrapheap. Case in point: curtains. Sure, until very recently it would have been hard to imagine this antiquated style being reborn, but here we are, all marching to the barbershop in unison with pictures of Timothée Chalamet clutched to our chests.

Today, the centre parting is much the same but the execution has changed. Back in the ‘90s, it was all about straight lines and smooth hair. This time, however, it’s all about messiness, texture and asymmetry.

Wraparound Shades

Fashion is cyclical and grimly predictable. No matter how much you want to believe a trend won’t resurface 20 years down the line, it invariably will. Wraparound shades are one such item. They were huge in the 1990s, but looking back from the 2010s, their comeback was less likely than Lance Armstrong’s.

Wraparound shades are back though, whether you like it or not. Aerodynamic-looking Oakley specs have been getting plenty of runway time over the last couple of years and they don’t look to be going anywhere soon. As to whether you should get involved or not, it’s very much down to personal taste and style. What we will say, though, is that they don’t lend themselves particularly well to more traditional menswear pieces.

Cargo Pants

Comfortable, practical and (depending on who you ask) stylish. What’s not to like? Sure, they took on some doomsday prepper vibes for a while and disappeared into fashion’s nuclear bunker, but thanks to the ongoing obsession with functionality and the great outdoors, cargo pants are very much back.

If you’re yet to be converted to the wonders of cargo pants, why not check out some of the more premium options on offer. Brands like Brunello Cucinelli and Monitaly are making some truly luxurious versions that are well worth a look.

Paddy Maddison

Paddy Maddison is Ape's Style Editor. His work has been published in Esquire, Men’s Health, ShortList, The Independent and more. An outerwear and sneaker fanatic, his finger is firmly on the pulse for the latest trends, while always maintaining an interest in classic style.