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.















Yellowman & Supercat
i voted for Cat, trust. Jesse is a hater.
what’s to hate about supercat? shabba for the next round..those glasses
yeah he definitely buss ragga-style on MTV with the frankenfade and the ripped clothes. but Cat definitely could pull the full range of 3-piece suit and spats, boops-daddy style to buffalo soldier bandana and everything in between. bad.
i also nominated the Ouch Girls, but noooo
I forgot to mention Carlene, the first Dancehall Queen
Hater? Super Cat is my favorite dancehall artist. Look, we’re a Caribbean culture website not just a dancehall music website. I tried to be democratic, in choosing people from different islands, and from different disciplines. Still, there’s 5 Jamaicans on here, 3 of ‘em artists. If it was a top 20 or a top 10 dancehall icons, all of the names mentioned in the comments would have made the list.
Did I say 5 Jamaicans? I meant 6.
fuck it im going rogue: here is my alternate reality tea-party Top 10:
Grace Jones
Bob Marley
Naomi
Che Guevara
Sidney MF Poitier!
Basquiat for bussing the suit & dreads style
Super Cat
Manolo Blahnik
Desmond Dekker
Rihanna
Honorebel mention: Harry Belafonte, Ouch Girls, Sinta Arunta-Bronte, Shabba, Dr. No
Sherman, Suze: weigh in!
No Jillionaire? That dude got style.
carlene? lady saw? ninja? nicodemus? jus sayin.
…and supercat should’ve totally made original list.
naomi and rhianna i can’t really co-sign on cuz they’re not responsible for their own sense of style. their peoples are. you can tell when its natural swag vs. un-natural.
How come Fidel Castro never made the list? I say tie up Jesse for a day and force him to listen to Milli Vanilli all day
Fidel made the real list–on devils advocate program i was saying maybe che is more of style icon, tho as Jesse pointed out mad hipster dudes are rocking the fidel beard these days. just for the record we are all (including Jesse) Super Cat superfans round here, i was just playin