2000s Fashion Is Back, and It Looks Way Better Than You Remember

If the return of 2000s fashion surprises you, it really shouldn’t. Every generation mines decades past for style inspiration, and it was only a matter of time before the hallmarks of Y2K style reared their bedazzled heads again. If you’re old enough to remember them from the first time around, don’t go poking around in your closet just yet: aughts-era menswear—the bootcut jeans, trucker caps, and rimless sunglasses that once dominated TRL—looks a little bit different than it did in its heyday. Over the last few years, 2000s fashion has experienced a serious glow-up, and the clothing aggregated below feels less like a straight Napster rip and more like a Top-100 remix. So consider this guide a highly-curated playlist of the genre, and let the hazy nostalgia wash over you like the dulcet tones of a Nickelback banger.

Big, Baggy Blue Jeans

Pre-distressed bootcut jeans caused a lot of pearl-clutching in the 2000s, but it didn’t take long before they dominated designer collections and mall brand stockrooms alike. And after a lengthy detour in the early 2010s, our latest stop on the fashion carousel has led to their resurgence. You can wear a pair a la the Biebs, but you can also clean ’em up by slipping into a spiffy striped button-up. The only key to pulling off a pair is knowing that big jeans beget big shoes—lucky for us, puffed-up skate sneakers are back, too. 

Gap boot jeans with washwell

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Acne Studios 2003 relaxed fit jeans

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Cool-Guy Cargo Pants

Cargo pants returned to the zeitgeist years ago, but the coolest pairs on the market today tap into the oversized proportions of the early aughts. You can always embrace their military roots alongside shit-kicking boots and a trim white tee, but for the full Y2K vibe, toss ’em on with lug-sole derbies, a paper-thin band tee, and one of those trucker caps immediately below. Your daily haul may no longer include a Nextel awaiting its next chirp (Google it!), but considering how much tech the average person is beholden to in 2023, cargos might be even more practical now than they were in 2003.

af cargo pants

Abercrombie loose utility cargo pant

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Our Legacy black mount cargo pants

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Nike ACG smith summit convertible stretch Cordura nylon-ripstop cargo trousers

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Corridor ripstop cargo pants

Eye-Grabbing Long-Sleeve Tees

Even two decades ago, there was nothing all that new about graphic tees—they’ve always been the method du jour to rep your favorite band, commemorate a charity 5K, or fondly remember the time your favorite band rocked out at a charity 5K. But at the dawn of the millennium, the decade’s long-sleeve tees were bolder, brighter, and more overtly in-your-face than ever before. Capital-D designer brands have since gotten in on the action, too, but today’s versions don’t really look all that different. If you want to tap into your inner sitcom heartthrob or pop-punk frontman, toss one on under a short-sleeve tee, pattern mixing be damned.

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We11done black horror college long sleeve T-shirt

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Saturdays SNYC x Moon Collective eyes long sleeve tee

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Parks Project great smokey mountains long sleeve T-shirt

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Dries Van Noten long sleeve oversized tee

Skateboard P-Approved Trucker Caps

Trucker hats were everywhere in the early part of the 2000s, protecting the domes of up-and-coming actors like Ashton Kutcher and legendary super producers like Pharrell Williams. And in 2023, they’re back in a big way. The rhinestone-embellished versions have mostly stayed in the past, but simple logo-adorned mesh caps are running amok and remain one of the easiest ways to imbue your fits with an All-American edge, whether you wear ’em with a tank top and jeans or as the rugged counterbalance to a slouchy suit.

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Katin vintage trucker hat

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Gallery Dept logo print twill and mesh cap

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Nahimas green & white trucker cap

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Filson logger mesh trucker hat

Ringer Tees With Some Oomph

The 90s and 2000s are to today’s youngsters what the ’70s and ’80s were to members of the previous generation. That’s how things like bootcut jeans (the 2000s riff on ’70s flares) got a second life, and why retro ringer tees went from banal gym class attire to expressive street style essential. Unlike the clean-cut sportswear versions of the more distant past, though, the ringer tees of the 2000s their 2023 homages are a little more colorful—and feature a lot more graphics. Wear yours with mesh shorts if you want, but a grungier fit complete with ginormous cargos and thrashed sneakers will give you that “playing hooky” edge.

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Dickies x Braindead embroidered T-shirt

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Adidas x Wales Bonner WB logo striped organic cotton T-shirt

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Heaven by Marc Jacobs back to school T-shirt

Polos That Really Pop

Among high school jocks and hip-hop impresarios swept up in the spirit of 2000s maximalism, candy-colored rugbies and doubled-up polos were de rigueur. Now the era’s signature staple is back in rare form as an essential ingredient of the neo-prep resurgence, ready to be paired with today’s oversized chinos and chunky derbies. Collar popping, as always, remains optional.

ralph lauren striped polo

Polo Ralph Lauren classic fit striped jersey polo shirt

j.crew polo

J.Crew classic polo shirt

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Drake’s navy, orange, green, and pink stripe cotton rugby shirt

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Mesh-Heavy Running Shoes

We’ve spent the better part of the year preaching the gospel of the retro running shoe. But if you’re still getting up to speed, here’s the gist: brands like Asics, New Balance, and Saucony are deploying silhouettes from their archives to consistently massive success. Sure, they look killer anchoring 2023’s wide-fitting trousers and baggy shorts, but they also retain the signature comfort that made them a hit in the first place—a win-win for style-minded dudes who grow a little more conscious of their podiatric health with each passing Supreme campout.

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Saucony OG Progrid Omni 9 sneakers

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New Balance 860V2 sneakers

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Adidas NSRC Exomniac cushion sneakers

Premiere-Ready Rimless Shades

The dawn of the 21st century ushered in tide of sleeker everything—slimmer cell phones, smaller music players, and, most importantly, minimal-leaning sunglasses that ditched the extraneous hardware entirely. Unlike the sporty mirrored wraparounds of the ’90s, these upscale sunnies looked—and still look—best with the trappings of a low-key daytime premiere, though they often boast gently-tinted lenses that promise round-the-clock wearability. Whether you’re getting down on the red carpet or just trying to imbue your black shoes and blue jeans with some early-2000s flair, these pared-down accessories are impossible to miss. 

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Bottega Veneta metal sunglasses

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Cartier men’s rimless rectangle metal sunglasses

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Ray-Ban RB4255 sunglasses

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