Y2k Style Guide: 2000’s Era Fashion Aesthetic For Guys

Last updated: December 26, 2021

During the 2000s, streets were filled with a string of styles that remain relevant even today. Fashion designers and trendsetters are always taking inspiration from the past for their upcoming collections, especially from the 2000s era.

Nowadays, there is nostalgia about this era, while y2k fashion trends are making a huge comeback. Leisurewear and casual clothing were the biggest trends in the early 2000s, giving rise to throwback jerseys, tracksuits, and shuttle pants in men’s fashion. 2000s Hip Hop Fashion is identified for its staple pieces such as grills, New era caps, Durags, cargo pants, denim jeans, polo shirts, tracksuits, Ed Hardy t-shirts, ribbed sweaters, Air force ones and basketball jerseys.

If you want to know everything about the major trends of the 2000s, here are the best tips & tricks. Keep scrolling to find out the best trends for men coming straight out of the 2000s.

Artist-Owned Fashion Brands

Brands such as Girbuad, Ed Hardy, LRG, Red Monkey, Evisu, AF1s, Outkast, Von Dutch, AVIREX, and Fubu were among the most prominent at that time.

By the time the 2000s came around, Hip Hop was becoming one of the biggest music genres worldwide; the genre’s commercial success would be reflected in the artists’ outfit choices & lifestyle.

Famous rappers were associated with their name brands, Jay-Z with Rocawear, T.I. with Akoo, Nelly with Vokal, e.t.c. Artists began creating their own clothing lines during the 2000s due to the success of their music.

Hip/Hop Style

Hip-hop has been at the epicenter of modern fashion for almost four decades. The changes that were propelled by hip hop have spurred fashion movements around the globe.

By now, hip-hop fashion was an actual thing defined by a certain set of principles that arrived directly from the streets it was born. Streetwear and hip hop would become one in the same thing, two halves of the same coin, and the 2000s solidified that in ways unimaginable.

Baggy oversized clothing became the norm and from this tradition, brands were birthed, such as Fubu, Ed Hardy, Academics, Phat Farm & Wu Wear. One of hip hop’s most visible trends continues to be the tall tees, wide-leg jeans, shuttle pants, oversized shirts, bandanas,and baseball hats.

Popular streetwear styles included distressed skinny jeans, loose-fitting t-shirts, tracksuits, hoodies, graphic t-shirts, vintage tees, and sneakers. Especially retro Nike Air Jordan’s, Adidas, and Timberlands.


The rise of Jeff Hamilton jackets arrived in the early 2000s and became the go-to outerwear choice. The 2000 starter kit for the jackets includes bomber jackets, cardigans and varsity jackets with patches of basketball teams.

Cargo Pants

One of the most iconic items of 2000s fashion was cargo pants. The ultimate street style look is oversized, baggy cargo pants paired with a tall tee or a crewneck sweatshirt and sneakers.

Double Denim

In the early 2000s, many celebrities wore Ed Hardy so naturally, it trickled down to the mainstream. Justin Timberlake and Britney Spears made iconic appearances wearing head-to-toe denim on denim. Tackle the denim trend by mixing different shades of denim, like a blue jacket with dark wash jeans or a white denim jacket with black jeans.


From slouchy velour to Adidas striped tracksuits, the athleisure mega-trend in clothing blurred the lines between the clothes you would sweat in during a workout and outfits you would wear to be seen in.



When it comes to accessories, in the 2000s, everybody just wanted really colorful stuff, gold chains, chunky necklaces, fitted hats with stickers on, and pinwheel hats. The motto was: the more colorful, the better. Durags are key items which have played a significant role in Hip Hop culture from the 90s and 2000s. The head accessory was mostly associated with 50 Cent, Jay-Z, Tupac, Camron, and Nelly to name a few. Similar to durag, the sweatband used became a staple piece for rappers.

Baseball Caps & Bucket Hats

In 1999 there was a high peak of the brand Von Dutch, with many celebrities rocking the trucker hats with the brand’s logo. Artists during the 2000s wore baseball hats in multiple ways, whether that be leaning the hat to the side like T.I, or pairing it with a durag like 50. Baseball caps can be found in multiple colorway options and can be styled with oversized clothing or a more tailored fit.

The bucket hat was already making waves in the 90s hip-hop scene, but in the 2000s, the popular hat became a mainstream fashion statement, like the iconic Kangol bucket hat. Kangol was one of the most famous headwear brands, and every notable rapper favored a bucket hat in various colors, prints and textures. For a more relaxed and cool look, opt for an oversized hoodie paired with sweatpants or chinos. Add some chunky sneakers and a vintage Ralph Lauren bucket hat for extra comfort and style.

Chunky Jewelry

By the early 2000s, exaggerated jewelry pieces were the trademarks of that era. Gold chunky necklaces, chains and rubber bracelets were a huge hit at that time. When it comes to timepieces, the bigger, the better. Big, bold-colored watches embellished with diamonds and gems reflected the spirit of the 2000s.


Air Force One

The Air Force One is probably one of the most iconic sneakers. In the 2000s, artists made the iconic silhouette a staple piece within their wardrobe from Nelly to Dr. Dre, wearing a pair daily.

Timberland Boots

Timberlands also had a massive involvement in hip-hop culture during the 2000s. Initially intended for construction workers, timberland boots found their way to urban clothing and were long associated with rappers and hip hop music. Dress them up or down with a pair of joggers and a tall tee shirt to go with the casual vibe. Add a bomber jacket to enhance the laid-back vibe.

Air Jordans

There’s no single shoe trend that’s more iconic from the Y2K era than high-tops from Nike. From “Midnight Navy” to “Space Jam”, Jordan sneakers have had their iconic silhouettes placed throughout the hip hop culture of the 2000s. Their flat-soled, high-top shape lends a retro appeal that feels really cool right now, while the brand has been releasing updated Air Jordan 1’s in fresh new color options.