2000s hip hop fashion

You had to be there. It may sound cliche, but it was true. In hip-hop as well as fashion, the 2000s were an era. Hip-hop fans often feel nostalgia when reflecting on the 2000s style and early oughts (especially between 2000 and 2005). They also laugh but have more questions than answers. There are questions like “Why Did We Wear That?” and “What Were We Thinking?” but also an appreciation. We appreciate that brands like FUBU and Sean John are available.

We appreciate that we lived through the Von Dutch period. It was appreciated that we put together some of our outfits, even though they look a bit chaotic in retrospect. Since many of these fashion trends were worn by hip-hop artists in their music videos, performances, and songs, they are also a great reminder of the good times in music.

We will look at 20 of our favorite hip-hop-style trends from the 2000s and why we love (and still love) them. Enjoy this blast from the past.

FUBU

FUBU. For Us, By Us. The FUBU fashiStyleend began in the 1990s but continued into the early 2000s. FUBU was not only worn by celebrities but also by us regular folk. The brand peaked in popularity when an album of hip-hop greats was released ( The Good Life (FUBU)). It is popular today and recently teamed up with Marvel for a Black Panther: Wakanda Forever collection.

Trucker Hats

Pharrell is partly responsible for the popularity of these hats. Back in the day, the artist was rarely seen without his trucker caps, which helped to spark the trucker cap trend among the skateboarding community. Pharrell is a pioneer when it comes to streetwear and skating.

Denim

Why did we millennials wear denim so much? Not only denim jeans but also denim jackets and hats. Denim skirts were also popular. Why did we wear so much denim? Who was the original creator?

Rocawear

For those too young to recall, Jay-Z’s first business venture was his streetwear brand Rocawear. It was a representation of everything “Roc Nation.” Custom Rocawear shirts, headbands, and the Roc Chain were available only to Roc Crew members. Rocawear is still a favorite among many because it reminds them of Jigga’s early 2000s albums.

Headbands

Allen Iverson was credited with popularizing the headband trend in the late 90s. Rappers would dress like him, wearing headbands, basketball jerseys, shorts, sneakers, and even basketball shorts. Nelly, a headband enthusiast at the time, also wore them. Bow Wow was also a headband wearer.

Grills

Nelly’s “Rob the Jeweler and tell them to make me a Barbecue” was a popular song in the mid-2000s.

Oversized T-Shirts

From 2000 until 2007, oversized t-shirts almost reaching your kneecaps were a big thing. You can think of videos like “Oh I Think They Like Me” or “Lean Wit, Rock Wit It” by Dem Franchize Boyz.

Jersey Dresses

Ah. The great jersey dress is gone. Jersey dresses were worn frequently by women in hip-hop. The two most famous examples are Mya’s Jordan Washington Wizards jersey dress and Mya’s video for “Best of Me,” where she appeared with Jay-Z in a vintage Jordan UNC Jersey dress. We all agree that Kobe Bryant wore the best jersey dress.

Basketball/Football jerseys

While basketball and football jerseys are now worn by sports fans regularly, the 2000s were the decade that made them cool to wear outside of games.

Durags

You can say what you like, but it wasn’t until the early 2000s that rappers such as Eminem and 50 Cent started wearing durags in public. This brings us to the next point.

Ballcaps and Durags

In the early 2000s, it was very fashionable to wear fitted caps on top of durags and tip them slightly to the side.

Sean John

Diddy’s Sean John clothing collection was a cultural moment. Sean John became one of the biggest Y2K brands in the early 2000s. Despite Sean John being a men’s clothing brand, women cut up shirts to make capris and jeans into capris. This was especially true in New York. Diddy and Missguided teamed up in 2021 to launch a women-only Sean John collection.

Bandanas

What was the early 2000s like without bandanas? Whether worn by DMX, Ja Rule, Aaliyah, or Eve, bandanas were a major early 2000s trend. They are now making a low-key comeback.

Air Force 1s

Air Force 1s had been a popular hip-hop song since 2001/2002, but Nelly took it to a new level in 2002 with “Air Force Ones,” a track from his Nellyvillealbum.

Timberlands

You had Jordans, Air Force 1s, Nike variations, Reeboks, and Timbs. (There were also some PUMAs and New Balances thrown in). Timbs (especially in NYC) were ubiquitous.

Pink

Cameron was the only one who wore pink. Nobody. Cam’ron wore pink jackets and pink sweatbands. He was determined to dispel the idea that pink is “too feminine” for men. Not only did he succeed, but soon the guys were taking inspiration from him. Real men wear pink. Period.

Chains

Another memorable moment of Y2K was the name/brand chains. They were often obnoxiously large. Usher wore him—the Rocafella Crew wearing theirs. Snoop Dre and Em are wearing theirs. Bad Boy and G-Unit are wearing theirs. Who in the 2000s didn’t wear branded chains at this point?

New Era Fitted Caps

New Era is still the most popular brand in 2023. We have already discussed the importance of fitted caps in the 2000s. New Era is the brand most people choose when buying a ball cap.

Baby Phat

The chokehold Baby Phat held on the women of the hip-hop community in the early to mid-2000s is hard to describe. You had Baby Phat tracks. Baby Phat jackets paired with low-rise jeans. Baby Phat jackets paired with UGGs. Kimora Simons deserves a shout-out for launching one of the most influential fashion trends.

Camouflage

Camo remains very popular, but the 2000s were the heyday of camo. We must remember the camo era from Destiny’s Child’s “Survivor” video, where they wore all camo, to Missy Elliott’s background dancers wearing it in her videos and performances.