In the early 1990s pop rappers such as left Eye of TLC, Kid 'n' Play, and The Fresh Prince made bright, often neon-colored clothing, and baseball caps popular.

Fresh Prince

TLC

Kid 'n' Play

Late R&B singer Aaliyah and TLC created a new fashion trend among women. They wore big flannel shirts, and oversized pants. They would also couple the oversized clothing with a tight shirt or sports bra underneath their big shirts. This was to display their own unique version of femininity, showing that everything does not have to be tight and form fitting in order to be sexy.

 Aaliyah

TLC

Kris Kross also established the fashion trend of wearing clothes backwards. 

And the brief trend of polka-dot clothing was sparked by Kwamé, while others still continued to wear their mid- 80s attire.

Kwamé front center.

Nike dominated the urban sneaker street wear market in the late 1980s and early 1990s.

                                                                          Nike 1980s

                                                                          Nike 1990s

Other clothing brands such as Carhartt, Reebok, Kangol, Timberland and Champion, were very closely associated with the hip hop scene. Particularly on the East coast with hip hop acts such as Gangstarr and Wu-Tang Clan sporting the look. 

Gangstarr in Timberland boots.

Wu-Tang Clan

Gangsta rap pioneers N.W.A popularized an early form of street Gangsta style in the late 1980s, from the Huslter clicks and African American Gangs who were there. Consisting of Locs sunglasses, Dickies pants, white T-shirts, Chuck Taylors sneakers with Raiders Starters jackets and black Raiders baseball caps.

N.W.A

Locs sunglasses

Dickie pants

Raiders Starter jacket

Chuck Taylor sneakers

 

Starter jackets were also a popular trend in their own right during the late 1980s and early 90s. They were seen as a status symbol, which caused theft of the jackets, which were reported in the media. 

Hip hop fashion in this period of time, also influenced high fashion designs. In the late 1980s Isaac Mizrahi, who was inspired by his elevator operator who wore a heavy gold chain. Showed a collection that was greatly influenced by hip hop fashion.

Isaac Mizrahi

Models wore black cat suits, big gold nameplate-inspired belts, gold chains, and bomber jackets with fur-trimmed hoods. The look was called "homeboy chic" by Womenswear Daily.

In the early 1990s Chanel also showed hip-hop inspired fashion in several shows.

Chanel model, in a hip-hop inspired outfit.

The hip hop trend however did not last long, designers quickly moved on.