Y2K's Most Influential Male Fashion Icons (2024)

Whether you grew up in the Noughties and aren’t quite ready for the return of low-rise jeans or you’re a Gen-Zer with a closet full of tracksuits, there’s no denying that Y2K fashion is making a triumphant return, inciting the same appeal and trendiness it did back in the 2000s. To provide you with some much-needed inspiration, we’ve curated a list of seven male cultural icons who made waves in the Y2K fashion scene, and whose iconic styles continue to influence contemporary fashion trends today.

Justin Timberlake

With his showy style and boy band charm, Justin Timberlake’s Y2K persona embodied the quintessential aesthetic of the 2000s. His bleached curls and infamous collection of fedoras immediately conjure images of the era’s fashion. Velour tracksuits, fur-trimmed collars, and tinted sunglasses were all staples in Timberlake’s wardrobe, epitomizing the trends of the time.

Perhaps his most iconic ensemble, however, is the double-denim suit he boldly rocked alongside Britney Spears at the 2001 American Music Awards. Love it or hate it, this look left an indelible mark on denim fashion trends in the 2000s. Remarkably, it remains a topic of conversation in the fashion community even today, more than two decades since its unforgettable debut.

Cornell Iral Haynes Jr. (Nelly)

The Y2K era saw an undeniable influence of hip-hop and rap on the fashion world, with artists like Cornell Iral Haynes Jr., better known as Nelly, at the forefront of this cultural shift. Much to the chagrin of their elders, teens worldwide were captivated by Nelly’s style, characterized by layered t-shirts, bandanas, durags, baggy cargo pants, and flashy jewelry.

The intersection of sports, hip-hop, and fashion has been brewing since the 90s, when rappers began donning athleisure and jerseys adorned with the logos of their favorite teams and athletes. Nelly’s infectious music was paralleled by his rapid rise to fashion prominence in the 2000s, catalyzing a surge in sportswear and urban-inspired streetwear trends that dominated the era.

Chad Michael Murray

Renowned for his brooding, bad boy image in “Gilmore Girls” and “Dawson’s Creek,” actor Chad Michael Murray seamlessly transitioned his iconic image from the screen to the fashion world. His fashion choices, featuring bucket hats, puka shell necklaces, and a penchant for goingsemi-shirtless, embodied the effortlessly cool vibe of the 2000s.

Even in more formal settings, Murray’s signature style shone through. His casual yet chic attire, with untucked button-down shirts, sneakers, baggy jeans, and open dress shirts layered over graphic tees were all go-to get-ups for the actor and encapsulated the more laid-back looks of the era.

Travis Barker

Travis Barker’s punk-rock, streetwear-inspired style was revered throughout the era by fans and fashionistas alike. Cut-off graphic tees, oversized shorts, and wraparound sunglasses were all typical clothing items for the Blink-182 drummer, exemplifying the rebellious spirit of the time.

Like Murray, Barker’s non-conformist approach to fashion extended beyond his everyday attire into more formal settings. His formal looks were just as irreverent and daring as his casual style, and they certainly didn’t stop at his clothing choices. Starting with his skin, a multitude of tattoos and facial piercings, combined with his signature mohawk and sometimes shirtless styles, were all integral components that contributed to his edgy and distinctive appearance.

Usher Raymond IV

Known for his remarkable talent and upbeat stage presence, Usher Raymond IV brought a unique perspective to the Y2K fashion scene. With a flair for fur and flamboyance, Usher’s style was anything but conventional. He had a penchant for infusing a sense of luxury and leisure into his outfits, even when sporting trendy pieces like denim overalls and oversized outerwear.

Usher was never one to shy away from experimentation, often playing with controversial combos and adding bold statement pieces into his wardrobe. Whether attending a casual party or a black-tie event, Usher’s audacious attire and casual confidence consistently left a lasting impression. His style, both on and off the red carpet, always shocked spectators and remained unmatched throughout the era.

Ashton Kutcher

Ashton Kutcher, best known for his goofy, fun-loving character in “That 70s Show,” effortlessly incorporated his on-screen persona into his personal style during the 2000s. His fashion choices often featured a trucker or bucket hat paired with playful graphic tees, mirroring the more lighthearted side of the era. Kutcher also had a love for layering, combining sweaters with collared shirts or donning blazers over t-shirts for a unique juxtaposition.

Though he had a fondness for clothing printed with amusing sayings, Kutcher’s infectious charisma transcended both the screen and his style. He was seldom seen without a smile, and his cheerful demeanor set him apart from many of his Y2K counterparts and added to his enduring Noughties appeal.

Dave Navarro

Jane’s Addiction guitarist Dave Navarro was a fearless fashion trailblazer during the 2000s. Unfazed by the spotlight, he unapologetically embraced androgynous clothing and outlandish costumes. His wardrobe often featured feminine scarves, skirts, and tank tops, challenging traditional fashion norms and defying stereotypes.

Navarro’s signature look was rarely complete without heavy eye makeup and an array of eccentric accessories. If diamonds are a girl’s best friend, then Dave Navarro’s unconventional attitude and misfit style were his closest companions during this era.

Y2K: an avenue for self-expression and creativity

Whether you’re enthusiastically embracing the Y2K comeback or quietly praying for its passage, it’s important to remember that fashion is, at its core, an avenue for self-expression and creativity. Trends come and go, but the joy of experimenting with styles, breaking boundaries, and leaving your own unique mark on the world of fashion remains a timeless endeavor. So, don’t be afraid to channel your inner Y2K icon and draw inspiration from the rebellious spirit, carefree charm, or unabashed audacity of these male fashion pioneers. After all, fashion should be about having fun and making a statement, and the Y2K era reminds us that the possibilities are endless.

About the Author: Cat Broughton

Cat Broughton is a creative lifestyle writer and fashion fanatic with a particular affinity for the free-spirited styles that dominated the seventies. She’s deeply passionate about all things vintage and enjoys experimenting with unique pieces that she finds at local thrift shops or in her parents’ attic. When she’s not putting pen to paper, you can usually find her perfecting her downward dog and sporting platform sandals, though usually not at the same time.