Words by Jesse Serwer

Already proclaimed a “style icon” by Paper, Complex and, yes, even Okayplayer, Theophilus London has fashion brands tripping over themselves to work with him right now. Watching the Brooklyn-born Trinidadian rapper/singer’s ascension into full-fledged it bwoy, we can’t help but notice that he takes many of his stylistic cues from fellow Caribbeans, from Jean-Michel Basquiat to Fab Five Freddy and Harry Belafonte. Between Theophilus’ emergence and his fellow Trini Anya Ayoung-Chee‘s show-stealing on Project Runway, Caribbean style seems to be having a little moment right now, so it seemed like the perfect time to count down the most iconic practitioners of style from the islands and the Diaspora.