When you’re the birthplace of hip-hop, of course you are also going to be home to some of the most gifted rappers of all time. We crowned the best New York rapper before and now, we’re looking at how the city’s legendary MCs stack up in the style department.
The highlights span decades. The ‘80s saw legends like LL Cool J and Run-DMC repurpose b-boy swag and introduce it to the masses. Then came the logomania craze, courtesy of Dapper Dan. The ‘90s showcased an obsession with Polo and Nike sportswear. By the turn of the millennium, many of the biggest rappers were dabbling with flashy luxury labels like Versace and some of the biggest acts were even promoting their own brands.
Throwback jerseys and Pelle Pelle leathers led the way to B.B. Simon belts and rockstar chains in the 2000s. Streetwear entered the fold in a big way in the 2010s. Nowadays, no one is surprised to see their favorite rappers fronting campaigns for luxury brands or attending the Met Gala. After more than 50 years, the history of hip-hop fashion in New York is a rich as the city itself.
Needless to say, detailing the best dressed rappers to ever hail from the five boroughs was no easy task. When determining the 35 MCs who put that shit on best, we factored in a few things. Was their wardrobe influential and did it spark trends across the city and hip-hop at large? Were their looks experimental? Did they pull off different aesthetics? Were they consistent or was their prime limited to a brief window of time? And do they have iconic outfits or moments that still make moodboards today?
From trailblazers like Big Daddy Kane and Kool Moe Dee to modern icons like ASAP Rocky and Cardi B, these are the best dressed New York rappers of all time.
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