Rapper and music producer Sean "Diddy" Combs is hip-hop's original mega-mogul, having branched out into movie and TV producing, acting, restaurant ownership and -- most notably -- fashion, since hitting it big in music in the 1990s. Combs launched Sean John in 1998, and the line quickly morphed from a basic urban label into an international brand and men's department staple around the world. His success as a fashion tycoon paved the way for Jennifer Lopez, Gwen Stefani and other musicians-turned-designers. Revenue for Sean John exceeds $100 million annually. Not too shabby for a side business.
Shawn "Jay-Z" Carter launched urban clothing brand Rocawear in 1995, with Damon Dash -- his partner in the influential hip-hop label Roc-a-Fella Records. The brand, which initially capitalized on rap's saggy, baggy look, has matured into a more trend-based lifestyle label with urban flair, offering plus-size clothing, accessory, fragrance and kids lines, along with its signature street wear. Jay-Z sold the Rocawear rights to Iconix Brand Group in 2007 for $204 million, but Beyonce's other half -- who personally prefers a classic tux to jeans -- retained his stake in the company and remains active on the marketing and product development fronts. Annual sales in 2008 topped $700 million.
Music producer (he produced Common's newest, "Universal Mind Control") and rapper (as part of N.E.R.D. and as a solo artist) Pharrell Williams brought edgy Japanese style stateside when he teamed up with superstar Japanese designer Nigo of A Bathing Ape to launch two luxury street-wear collections: clothing line Billionaire Boys Club and sneaker brand Ice Cream, in 2005. Marrying limited-edition manufacturing runs with luxury fabrics, high prices and plenty of hip viral marketing, the collections were coveted from the get-go -- thanks also to Williams' image as a hip-hop eccentric who's as comfortable on a skateboard as he is in the studio.
Kanye West's forthcoming clothing label, Pastelle, has been in the works for more than two years now -- prompting fans to wonder whether it's ever going to see the light of day. (On his website, he promises it's coming this year.) In the meantime, hip-hop's king of high fashion -- who once said he considered himself a designer first and a rapper second -- has collaborated with Louis Vuitton on a series of limited-edition sneakers (out this month) priced north of $800 a pair and has teamed up with Ksubi for a collection of spacey sunglasses for Pastelle. But West's main contribution to fashion may always be his quirky '80s-inspired personal style. Who else can pull off a faux-hawk with a mullet or a collegiate jacket with a bow tie?
-- Emili Vesilind