2000s Hip Hop Fashion

Written By Bakes

Avid writer on Men's Hair, Grooming, and Lifestyle!

This is a sponsored editorial in partnership with GS JJ 

By the time the 2000s came around Hip Hop was becoming one of the biggest music genres worldwide, the commercial success of the genre would be reflected in the artists outfit choices & lifestyle. 2000s Hip Hop Fashion is identified for its staple pieces such as grills, New era caps, Durags, baggy t-shirts, air force ones and basketball jerseys.

In response to Hip Hops rapid commercial success during this time period record labels began to release bigger video budgets and label deals to artists allowing them to showcase these styles on all platforms whether that would be music videos, MTV Cribs, Award Shows, Magazines or on tour. The influence of 2000s Hip Hop Fashion continually presents itself today which is why our editorial will examine the best brands, trends and styles during this decade.

2000s Hip Hop Fashion (Brands, Trends & Styles)


2000s hip hop style

Grills came into prominence during the early 2000s with rappers choosing to flaunt their wealth by showcasing dental jewellery.

As we mentioned before rappers became accustom to bigger label budgets & commercial success, this in turn meant a flashy showcase of wealth, grills is one of the best example of this and a true 2000s Hip Hop Fashion Trend.

Mostly associated to southern Hip Hop artists at the time due to most artists sporting grills coming from Atlanta and Houston. Nelly can be credited for making Grillz more mainstream with his song Grillz featuring Paul Wall, Big Gipp, and Ali.

Baggy Clothing

baggy clothes hip hop

A huge part of 2000s Hip Hop Fashion was the exaggerated baggy clothing most artists wore from baggy t shirts and baggy jeans.

To take a quote from our 90s Hip Hop Fashion editorial

“Culturally oversized clothing became the norm which was often referred to as urban fashion and from this tradition brands were birthed such as Fubu, Phat Farm & Wu Wear catering to their audience of similar tastes.”

As the years went on baggy clothes went out of fashion with artists choosing to wear more fitted clothing. Today the appeal can be seen with the combination of baggy and fitting clothes. For example, a baggy hoody with a slim pair of jeans. This is a prime example of 2000s Hip Hop fashion presenting itself it subtle ways in contemporary times.

Custom PVC Patches

custom pvc patches

In addition to this many hip-hop lovers like to wear custom pins or PVC patches on their jeans, hats, backpacks, etc to show a personalized style and the favor of the culture. When organizing some group activities or establishing an organization, the custom pins or patches with the logo or slogan are more of a symbol of group identity.

Air Force Ones

The Air Force One in popular culture is probably one of the most iconic sneakers, this without doubt has Hip Hop to thank! During the 2000s artists made the iconic silhouette a staple piece within their wardrobe from Dame Dash to Dr Dre wearing a pair daily.

Not only did Nelly help to popularise grills but also played a huge hand with commercialising the Air Forces.

To take a quote from our how to wear air force 1s article

“The air force one has been designed in such a way that combines great looks with simplicity. Due to the surface area of the sneaker being wide many custom shoe designers naturally opted to make the air force one the default shoe to create custom designs on, Nelly made a song about the shoe which made them quickly culturally sought after”

Football/Basketball Jerseys

hip hop jerseysImage source – XXL

Throughout Rap & Hip Hop culture sports jerseys have always appeared in music videos with the artist often representing their home team. This was heavily apart of 90s Hip Hop Fashion which continued into the 2000s.

The connection between sports, athletes and hip hop has become seamless over the years for example

  1. The classic Allen Iverson and Jadakiss Reebook commercial

Prime example of cross breeding sports and hip hop culture. The admiration and respect between rappers and athletes is the reason we continued to see artists sporting jerseys in music videos.

Timberland Boots

timberland boots

Hip Hop took a regular boot created with construction workers in mind and turnt the silhouette into one of the most fashionable feet pieces worldwide. Timberlands to this day is one of the most recognisable footwear and had a massive involvement in the hip hop culture during the 90s and 2000s.

To quote highsnobiety – How Timberlands Became an Icon of Hip-Hop Style

“Timberland never intended for their boots to be worn by rappers, and found the association so far removed from their blue-collar roots that they at first tried to distance themselves from their new-found “urban” audience. But like so many brands who found popularity in places they didn’t know existed – Converse, Dr. Martens and Vans, to name a few – the subculture association has become such a large part of the brand’s identity that today that it’s hard to imagine them without it.”

During this period 2000s hip hop fashion as we mentioned saw artists sporting baggy clothes, which therefore meant jeans covering a large portion of the boot.

Artist owned Urban Clothing Lines (Rocawear, Sean John, G unit Etc.)

urban clothing

During the 90s rappers could be seen sporting multiple urban brands from Karl Kani, Lugz, FUBU and Pelle Pelle which created and marketed apparel to the urban market and demographic.

Artists such as 50 cent, Diddy & Jay-z would begin creating their own clothing line which featured heavily in music videos as a form of marketing and promotion. Though Rocawear and Sean John were formed in the 90s the brands saw a great level of success in 2000s being sold to other companies for millions. Other artists such as 50 and Nelly also created clothing lines during the early 2000s due to the success of their music.

Rappers began using this as a brand extension opportunity to further increase revenue and sales which proved to be successful during this time period.


durags in hip hop

Durags are more than hair maintenance accessories to keep hair frizz free & to preserve waves, Durags are cultural items which has played a significant role in Hip Hop culture from the 90s and 2000s.

During the 2000s the head accessory was mostly associated with 50 cent, Jay-z , Memphis Bleek, Camron, Mobb deep, Chamillionaire & Nelly to name a few.

The Durag today still appears in artist’s visuals and continues to be a cultural piece, highsnobiety covered the Durag Significance in modern times.



A large part of hip hop culture involves taking something, recreating it and giving it new meaning. Whether that be timberland boots originally intended for construction workers or old music used in samples to create new hip hop music. The sweatband is no different, the accessory created and used with the intention for athletes on the tennis court soon became a great alternative to caps for rappers.

As we previously mentioned, the connection between sports, athletes and hip hop has became seamless during the 90s & 2000s which resulted in artists incorporating sports apparel into their style, the sweatband being one of them.

Rappers from Nelly, Jay-Z, M.O.P, Tony Yayo amongst many others helped popularise the style during the 2000s.

Trucker Hats/Skate Culture

The friendship between Pharrel & Nigo (Founded of Bathing Ape) would see the growth of skateboard culture being incorporated into Hip Hop.

A video perfectly depicting this style would be Pharrel’s frontin which would perfectly merge the 2 sub cultures, skate and hip hop.

Trucker hats symbolised a different way of doing things outside of the traditional fitted caps.

Smart Casual/Back Pack Rap

backpack rap

Smart Casual and slim fitting clothes would run parallel and in contrast to the traditional baggy clothes in the early 2000s. What’s interesting about slim fitting clothes in hip hop culture is that it started as an alternative only favoured by a small group of people, towards the end of the decade this style would be mainstream and would phase out baggy clothes.

This style could be seen on artists such as Andre 3000, Kanye West and Pharrel. The influence of slim fitting apparel would influence a slim fit style towards the end of the decade, this influence can be credited to artists during the early 2000s willing to try something new with a need to stand out!


camron pink fashion

We’re giving Camron all credit for the rise and popularity of the colour pink and its use in Hip Hop during the 2000s. Prior to Camron artists chose to style outfits in more dark colours, Cam would break this tradition during the early 2000s by wearing pink, a bold statement as Men wearing pink in urban culture would be labelled effeminate due to the colour’s close association with women. Cam didn’t care about public criticism or scrutiny and would style pink in such a way that influenced hip hop males to incorporate pink in their outfits.

Camron’s Pink Influence in Hip Hop continues to manifest itself today & artists such as Kanye West have paid homage to Cam for popularising the style and colour. 

Exaggerated Jewellery

hip hop Jewellery

By the early 2000’s hip-hop and corporate America were in business and the genre had been commercialised. As the status of rap and its artists evolved, so did the jewellery, how so? With artists creating exaggerated jewellery pieces to flaunt their success & wealth.

The most notable examples during this time period

Camron’s Harlem world chain, Kanye West Horus Chain, T Pains Big Ass Chain, Soulja Boy’s the world is yours chain, Lil john’s Crunk aint dead chain, Pharrell’s Nerd Chain and Rick Ross Face Chain.

If there’s one thing that’s guaranteed its artists stunning with exaggerated jewellery pieces.


rappers wearing jordans

Jordan sneakers have had their iconic silhouettes placed throughout hip hop culture from the 80s when Michael Jordan first debuted his basketball career which only continued to grow throughout the 90s and 2000s.

Hip Hop music videos during the 2000s essentially became free marketing and promotion for the brand as we saw countless amount of artists sporting the sneakers within music videos.

As a result of this free marketing they boomed in popularity which made them a continued household name and brand. As we already mentioned the air force one on the list it would be worth mentioning that the 2 sneakers were rappers favourites.


bandanas in hip hop

The paisley print has been worn throughout Hip Hop since the 80s and has represented style, gang affiliation and fashionable headwear.

rappers wearing bandanas

Whilst the bandana has always been apart of Hip Hop we mostly saw it rise in popularity thanks to the likes of Nate Dogg and Tupac in the 90s and Juelz Santana in the 2000s.

Baseball Caps


Similar to the sports jerseys whether that be basketball or baseball jerseys, the baseball cap allowed rappers to represent their respective cities and hometowns.

The rise of hip-hop and its influence on style and pop culture resulted in the baseball cap being used primarily for its head protective qualities into a fashion statement. The baseball cap served multiple purposes which artists took a liking towards

  1. Multiple colourway options
  2. Great Fit and quality
  3. Opportunity to rep city/team

For these reasons above 2000s hip hop were filled with baseball caps (Another piece apparel that benefitted from Hip Hops free marketing and promotion)

Artists during this period were accustomed to styling the hats in multiple ways whether that be leaning the hat to the side like T.I, pairing it with a durag like 50 or rocking it backwards!

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