Noughties Style: The 2000s Men’s Fashion Pieces Staging A Comeback

Image Credit: Von Dutch

If you’re old enough to remember Britney and Justin in head-to-toe mid-wash denim (cowboy hat included), you’d be forgiven for thinking Y2K fashion couldn’t possibly make a comeback. But you’d be wrong. The 20-year trend cycle truly is unrelenting, and as Gen Z in particular looks to the past for style inspiration, many of the era’s most memorable pieces are creeping back into the sartorial spotlight.

As the younger generation thrift themselves silly, many of the hottest items are ones that were popular at the turn of the Millennium. The baggy jeans, the rimless shades, the cargo pants – hell, we’ve even seen the odd Von Dutch trucker cap resurrected from wherever they spent the last two decades hiding. But noughties style isn’t all bad, so what are the pieces worth working back into your wardrobe?

Here’s our pick of the 2000s fashion pieces you can theoretically style with success. Granted, you should probably avoid wearing all of them at once unless you’re heading to a fancy-dress party as all of the Backstreet Boys, but if you’re willing to proceed with caution, these are the garments and accessories to know.

Baggy Jeans

Hating on skinny jeans is almost passé at this point, but in case you’ve missed the biggest legwear news of the last five years, baggy is the current default setting for cool-kid pants again. There’s been a return to the oversized skater denim of the 2000s, and a sharp pivot away from anything even remotely fitted. And while we’d urge you to give overly baggy styles a wide berth, there is certainly something to be said for embracing a roomier fit now and then.

To dip a leg into this trend without embarrassing yourself, a good option is to go for a loose or relaxed-fit jean as opposed to anything too baggy. This way, you can reap the benefits of that extra legroom without going full Limp Bizkit, and experiment with the wider silhouette in a mature, timeless manner.

Oversized Hoodies

In the same vein, slouchy oversized hoodies and crew necks are the new mid-layers of choice for those who have their finger on the pulse. We’re talking boxy cuts, dropped shoulders and plenty of room in the body. It’s another look borrowed from 2000s skate culture, but you need to get your proportions balanced to pull it off.

The biggest mistake you can make here is to team an oversized hoodie with skinny bottoms. This creates a sort of top-heavy ‘chicken-leg’ effect that’s neither flattering nor fashionable. Instead, opt for a straight-leg or loose-fit alternative, and keep the footwear on the chunky side too.

Wraparound Shades

Super-streamlined aerodynamic eyewear was all the rage back when Myspace and MSN ruled the internet. But in the years that have passed since, the only people wearing these sorts of shades seriously were off-duty cops at BBQs. That all changed in the last few years when they began to experience an unprecedented resurgence.

That being said, pulling a pair of wraparound shades off in a stylish manner is no easy feat. If you’re going to do it, the best way to nail it is as part of a gorpcore-inspired outfit. Think cargos, trail runners and a fleece or shell jacket. Even then, they’re not the simplest of shades to style well.

If you’re in any doubt, stick to classic shapes instead.

Trucker Hats

In terms of headwear, nothing came close to the popularity of the humble trucker cap in the 2000s. With their foamy front panels, mesh backs and snap adjusters, these lightweight hats were the headgear of choice for everyone from A-list celebs to fashion industry insiders, before trickling down to civilian wardrobes around the world.

Now, thanks to the return of Y2K styles, trucker hats are back in force. From niche Japanese menswear labels like Kapital and South2 West8 to the biggest high-fashion brands, everyone seems to be revisiting this noughties favourite, so maybe it’s time you did too.

Tinted Shades

One of the easier Y2K styles to incorporate into your wardrobe is a pair of tinted sunglasses. Instead of going full blackout, these shades have fully transparent lenses with a hint of colour to them – usually yellow, brown, blue or green. It’s an easy way to add a subtle touch of character to an outfit, and they can be worn all year round.

The key difference between 2000’s tinted shades and the ones that are in at the moment is down to the frames… or lack thereof. Back then, rimless sunglasses were the height of fashion, but today it’s all about thick acetate styles that frame the face.

Check out Gucci for some of the best, or CHIMI for something slightly more affordable.


Yes, Uggs. No, really. These fleece-lined booties were everywhere in the 2000s, and now thanks to the power of influencer marketing, they’re shuffling around city streets once again. Hot on the similarly clumpy heels of Crocs, Ugg Boots are the latest ‘ugly’ footwear style to be experiencing a resurgence. And if you thought they were just for girls, think again, because a surprising number of male Hollywood stars, rappers and tastemakers have been spotted rocking them in recent years too.

We don’t blame you if you don’t fancy donning a pair in public, but in the post-covid era of the house shoe, there’s no reason not to have a pair on standby for chilling at home. Whether you choose to leave the house in them or not is up to you.

Webbed Belts

No self-respecting noughties skater boy would have considered himself fully dressed without an oversized webbed belt to cinch his jeans’ waistband around his buttocks. Worn with the loose end dangling in front of the crotch, these simple canvas belts are back in a big way, and they’re a nice simple option for keeping your casual pants up when you don’t fancy wearing a leather belt.

These belts are great because they’re infinitely adjustable. You aren’t restricted by pre-punched holes – you can simply shorten and lengthen it freely. And, contrary to popular belief, you don’t have to wear them flopping around at the front. Tuck the loose end into your belt loops and what you’ve got is a subtle and affordable casual belt that’s perfect for everyday duties.

Mesh Runners

You know the ones: lightweight, lots of metallic silver panelling and even more mesh. They’re the shoes you were wearing for PE in 2001, and now they’re back to take your casual wardrobe too.

Mesh runners are the ultimate 2000s sneaker, and they’re huge in the fashion world right now. This has been helped along by a string of extremely hyped collabs, including the Asics x Jjjjound GEL-Kayano 14 and the Aimé Leon Dore x New Balance 860v2.

They’re super comfortable, easy to style and go with anything from trackies to tailored pants.

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.