Even in the genre’s early days, back before MC Lyte rapped “Funky fresh, dressed to impress, ready to party” in 1989, hip-hop and fashion have been inextricably linked. From the old school to the new, whenever rap is mentioned, an image springs to mind of a character decked out in the latest “urban streetwear.” Depending on the era and region you grew up in, that might mean an Adidas tracksuit with a Kangol bucket hat, or an oversized Polo sweater with Girbaud jeans and Timberland boots (unlaced, of course). Maybe it conjures visions of a crisp pair of Dickies Khakis offset by Nike Cortez, or the Gucci button down with Filas.
From XXXL white tees with baggy denim, to off-white skinny jeans and one-of-one Supreme windbreakers, hip hop has always had its own look — separate from yet influenced by mainstream culture. In turn, the mainstream watches hip-hop like a damn hawk, making adjustments based on what rappers rock on album covers and in magazine spreads (behold, the ubiquity of basketball sneakers worn with street clothes). This relationship isn’t low key, either. Rappers now have their own fashion shows in New York, Paris, and Milan, and top design houses look to dress artists like Nicki Minaj and Kanye West for the red carpet. And while there have been missteps — Kriss Kross’s backwards jeans and Puff’s shiny suits spring to mind — one thing is for certain: From the very first basement parties in the Bronx to loft parties around the world, the number one rule for rap has always been to show up looking to turn heads.
In honor of this longtime love affair, we picked five iconic moments when hip-hop made style history.