The Biggest Trends in 90s Hip Hop Fashion


Since the 1990s, rappers have worn clothing with loose fitting designs – it remains an essential aspect of hip hop culture today. Combine oversized clothing with Timberland boots and finish off your look by adding a sleek chain for maximum effect.

Jerseys are also an iconic component of hip-hop fashion, as they allow fans to support a team or player while acting as status symbols. Drug dealers wore gold rope chains before becoming trendy accessories in hip-hop culture.

Baggy Tees

Baggy shirts were one of the signature pieces in 90s hip-hop fashion. Seen on both men and women alike, this oversized style often featured a large belt, and Timberlands was seen as a symbolic look from urban street culture in rap culture. This style remains highly fashionable among rappers, athletes, pop culture figures, etc.

Another 90s fashion staple was the bucket hat, worn by both women and men. More of a fashion statement than a functional hat, its popularity amongst younger hip hop artists inspired numerous streetwear looks; and you can still find this style available for purchase today if you want to relive that 90s hip hop fashion look.

Oversized jerseys were an integral part of 90s hip-hop fashion, often worn to represent one’s team or favorite player. This connection between sports and hip hop could be seen through music videos featuring jerseys like Jay-Z’s Money Ain’t A Thang and Will Smith’s Summertime, which prominently featured such attire.

Denim dungarees were an iconic fashion trend during the 90s, made most famous by Will Smith on The Fresh Prince of Bel Air. Female rappers adopted them too, and many rappers such as Tupac Shakur and Public Enemy used their attire to spread political messages through wearable political statements. Military camo was also widely worn then and can still be worn by rappers such as Biggie Smalls and Das EFX today.

The Native Tongues movement founded by artists such as Afrika Bambaata of the Universal Zulu Nation, A Tribe Called Quest, De La Soul, and Queen Latifah had an immensely positive effect on young people, inspiring bold creativity while advocating pro-black, Pan-African, and Afrocentric concepts, positive thinking, and spirituality. Clothing featuring tie-dye prints such as tie-dye, paisley patterns, or African wax prints was integral to this movement.

In 1989, Daymond John created the legendary global brand known as FUBU. Renowned for their vibrantly-colored, high-quality sportswear known for being fashionable yet sporty, edgy designs, they eventually sold over 500 million garments and garnered hundreds of millions in revenue, making this an impressive accomplishment for an independent family-run business.

Timberland Boots

Timberland boots were one of the main trends of 90s hip-hop fashion. Although initially created for construction workers, they soon became the go-to footwear choice among hip-hop artists from East Coast rap groups and east coast artists. Worn with various clothing pieces – from baggy hoodies and baseball caps to baggy shorts – these boots became part of urban culture and resilience symbolism – it wasn’t uncommon to see rappers sporting Timberland boots alongside baggy clothes like baggy denim jeans!

Timberland boots were an iconic part of gangsta rap culture, and as its popularity among drug dealers was glorified through this genre, Timberland boots became popular within its fan base. Customized with sports team logos or brand emblems further added to their street appeal; these boots became worn by famous east coast artists like Jay-z, Tupac, and Mobb Deep; moreover, they were frequently chosen as footwear by hardcore rap groups such as Boot Camp Clik from Brownsville Brooklyn as well as Wu-Tang Clan.

Timberland boots were often worn with baggy jeans, t-shirts, and hoodies that bore the names and logos of various gangs and groups that dominated the rap scene at that time; many featured the names or logos of groups or teams prominent in rap music at that time – these hoodies allowed black community members to express unheard political, social and economic opinions that otherwise would remain unsaid; other clothing used to show affiliation included baseball caps or bandanas.

Unlike T-shirts and hoodies, sports jerseys were another fashionable item among 90s hip-hop communities. This was because many top rappers from that era were affiliated with various professional sports teams and cities; wearing such jerseys became an excellent way to represent their heritage and identity on stage and off it. Some notable athletes to wear sports jerseys during that era included Notorious B.I.G, LL Cool J, and Aaliyah as examples of such athletes wearing such apparel.

Starter jackets gained widespread favor within hip-hop culture as an apparel item for both men and women. Wearers included notable artists like The Notorious B.I.G, Wu-Tang Clan, and LL Cool J – now seen wearing them are Kendrick Lamar and Rihanna!


Graffiti art is any piece involving writing, painting, drawing, or scratching art on walls, fences, buildings, and other surfaces without permission and public view. Graffiti can range from simple text messages to elaborate wall paintings and is typically considered vandalism but has also become known as an artistic form of expression.

Graffiti can also serve as an instrument of political and social activism, like Keith Haring’s use of graffiti to comment on drug addiction and HIV/AIDS; or Tatyana Fazlalizadeh’s messages against gender inequality – making graffiti an engaging form of self-expression that has immense power and influence.

One of the significant influences on 90s hip-hop fashion was gang culture, which resulted in one of the main subgenres of rap music at that time: Gangsta Rap. Gang culture then had an enormous effect on fashion among rappers and urban youth at the time – including an increasingly common trend of bandana-wearing as part of gang clothing, an easy way for members of any particular inner city gangs to show their affiliation in both music and clothing choices; popular with three teams: LA Bloods wearing red bandanas; East Coast Crips wearing blue; Chicago Latin Kings wearing black-and-gold bandanas as part of their attire.

Gangsta rap and its associated fashion were heavily influenced by African-American culture and black nationalism, leading to fashionable garments like kente cloth shirts, turbans, and dreadlocks becoming trendy trends in urban America. Musicians such as Tupac Shakur and Public Enemy used their music as a form of activism against social issues that affected urban America through song.

As the popularity of rap music increased during the 1990s, graffiti became more prominent in public spaces. This inspired more artists to move away from text-based works and instead include images and symbols in their pieces for a more sophisticated approach to graffiti art – pioneered by Jean-Michel Basquiat and Keith Haring, respectively. Nowadays, graffiti can be found almost anywhere imaginable – such as train and subway cars, bus shelters/stops; billboards; street and freeway signs; school/business buildings; park benches/fences, or vending machines/lockers/garages!

Big Brands

One of the hallmark trends of 90s hip-hop fashion was rappers’ embrace of big brands. This trend was driven by rappers’ perceptions that many such labels served as status symbols; this was particularly prevalent when it came to sportswear brands; therefore, it wasn’t uncommon to see rappers wearing NFL, NBA, and NHL jerseys with team logos prominently displayed – particularly oversized jerseys from these leagues with starter brand caps with team branding popular among artists like Eazy-E or Tupac rocking Los Angeles Raiders caps from Starter!

Kangol became synonymous with hip-hop culture because LL Cool J made its iconic presence known through his use of it in many seminal movies from that era, such as New Jack City (1991). Along with producing hats, Kangol also offered caps and sweatshirts, which became highly coveted within rap circles.

Rappers could often be seen wearing baggy t-shirts adorned with large belts and Timberland work boots; this was popular because it allowed them to show off their gangster persona without appearing too casual; moreover, this attire helped show their hometown pride, which became particularly evident with rap supergroups such as NWA and Wu-Tang Clan representing their cities on and off stage.

Will Smith first made denim dungarees famous when he donned them in The Fresh Prince of Bel-Air; their gangster chic style became widely worn among rap groups like Boyz II Men and MC Hammer. Additionally, check flannel shirts were widely worn among rap and grunge music groups due to their classic aesthetic and adaptability; they were either loose-fitted with one strap undone or slim-fitted and worn with a white tee underneath for versatility.