From baggy jeans and bling blings to classic gangster-inspired suits and bowler hats, a distinct and evolving fashion style has always been an indispensable element of the hip hop industry. Hip hop fashion traces its roots to the clothing style of African-American youths. Since then it has drawn its influences from hip hop scenes in different parts of the United States, from California to New York, as well as from various elements of underground and popular culture.

One of the earlier clothing styles in hip hop was the sportswear coupled with conspicuous jewelry which became the signature look for old school rap. Tracksuits, bomber jackets, berets, Doc Martens, and sneakers were some of the common apparel then. Men sported gold chains while women wore large gold earrings. The sports apparel of Adidas, Nike, and Le Coq Sportif were some of the commonly patronized brands in the 1980s. The 1990s saw the growing popularity of more sportswear from Tommy Hilfiger, DKNY, Polo, Calvin Klein, and Nautica. This particular fashion style became known as the urban streetwear and was further supplied by such brands as FUBU, Ecko Unlimited, Walker Wear, and Boss Jeans.

The emergence of gangsta rap as a sub-genre of hip hop fueled another fashion statement, this time inspired by the clothing styles of street thugs and prison inmates. Gangsta rappers started wearing baggy pants, bandannas, and tattoos. Not a few conservatives reacted negatively to the sagging pants and low-hanging waistlines. A religious group tried to combat the fashion style by giving out belts while others sought to make it illegal.

Other hip hop personalities opted for the classy gangster look and wore double-breasted suits, bowler hats, silk shirts, and alligator-skin shoes. This Mafioso-inspired image was popularized by the Notorious B.I.G. and Sean Combs a.k.a. Diddy, with the latter becoming known as the Shiny Suit Man.

Recent trends in hip hop apparel show the influence of hipster and preppy styles. Oversized shirts were replaced with tighter-fitting short-sleeved shirts, tracksuits were traded for sports coats, and tighter denims were favored over sagging jeans. Some of the popular accessories are large belt buckles and skull and skeleton ornaments. Decorated hoodies, fitted caps, and trucker hats are also commonly worn.

Heavy jewelry has also become an enduring mark of hip hop fashion, symbolizing an ostentatious display of fame and wealth. Known in hip hop slang as bling bling, these flashy accessories became ubiquitous fashion icons and common semiotic elements in a lot of music videos. Gold jewelry was the craze in the 80s but it was eventually edged out by silver and platinum. Grills or removable metal teeth coverings also became popular among celebrities.

With the development of hip hop fashion, rap artists eventually ventured into the clothing business and started producing their own labels. The rap group Wu-Tang Clan has its Wu-Wear, Damon Dash and Jay-Z have Rocawear, and Diddy has Sean John. Diddy also bagged the 2003 Menswear Designer of the Year Award given by the Council of Fashion Designers of America. Other hip hop personalities with their own clothing lines are Eminem, 50 Cent, Russell Simmons, Kimora Lee Simmons, and OutKast.