Toppa Top 10: Top 10 Caribbean Style Icons

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.

10. Lola Falana/Celia Cruz

Although their contributions to style are somewhat overlooked today, these two Cuban ladies blazed trails for dark-skinned women in the 1960s and ’70s. Born in New Jersey to a Cuban father and African-American mother, and discovered by Sammy Davis, dancer/actress Lola Fulana was the first Black woman to model for a line of cosmetics (Tigress by Fabergé) that was not targeted solely at Blacks, one of the first Black women to pose for Playboy and, in the late ’70s, one of the biggest draws in Vegas. The Queen of Salsa, Cruz was just as renowned for her bold wigs and hairpieces–which were just as unpredictable in terms of color, cut and texture as Rihanna’s are now–though she would embrace her African roots, too, rocking an Afro and cornrows, in the ’70s. Always larger than life but never cartoonish, there was nothing subtle about her style.

9. Desmond Dekker

One of the original proponents of rude boy style and a demi-god to the mods and skinheads who were the first adopters of Jamaican music in Britain, the late ska/rocksteady pioneer Desmond Dekker was known for his trademark beret, always kept cocked to the side.

8. Rihanna

Quickly shedding her innocent girl from Barbados act, Rihanna set the stage for Lady Gaga and Nicki Minaj (who was pretty close to making this list as well) in the mid-to-late 2000s, making avant-garde stage costumes and high concept fashion spreads a requirement for A-list female pop stardom. On a broader level, she’s had a bigger impact on women’s hair than anyone since Jennifer Aniston.

7. Gerald “Bogle” Levy

The Jamaican choreographer behind the Bogle, World Dance and Wacky Dip among other steps, Levy was the person responsible for introducing punk-rock fashions—spikes, studded belts, bleached hair—into dancehall more than a decade ago. Six years after his murder at a Kingston gas station, the look—as well as the dance step-driven songs that he was responsible for inspiring—remains as prevalent as ever.

6. Patra

Patra had some fairly big hits in the ’90s but she’ll always be best known for her thick, “Patra braids,” the inspiration for a major women’s hair trend in the early-to-mid 1990s. She was still rocking them when we caught up with her last month for her first interview as she hits the comeback trail.

5. Jean-Michel Basquiat

Another iconic U.S.-raised figure whose Caribbean background is often overlooked, the Brooklyn-born artistic genius was the son of a Haitian immigrant father and a fourth-generation Puerto Rican mother.

4. Naomi Campbell

While our fashionista friends cast some doubt on her personal taste level, as the greatest supermodel of all-time Naomi Campbell has been the muse for many of the most experimental—and a lot of the most accessible—fashions of the last quarter-century.

3. Fidel Castro

The cap, the beard, the fatigues—Castro has, arguably, the most identifiable signature look of any modern political leader. And while he was fading from official view due to his health problems in the 2000s, his trademark, square-brimmed olive cap—the “Castro hat”—became a staple of hipster fashion, stripped, for the most part, of its political connotations. Echoes of the Castro aesthetic can be found in the military-inspired garb worn by many reggae artists in the late ’70s.

2. Grace Jones

The dictionary definition of style icon, the Jamaica-born, New York-raised, Europe-based model turned singer turned actress turned enigma might have made No. 1 on this list if she didn’t transcend ethnicity and geography. That’s not to say Grace Jones doesn’t rep her culture as much as any Caribbean on the world stage: just cue up “My Jamaican Guy” or any of her reggae-flavored 80s collaborations with Sly and Robbie and Chris Blackwell. MIA through much of the ’90s and 2000s, the 63 year old has returned in a big way in the last few years, most notably as a reference point/inspiration for Rihanna, Nicki Minaj, Lady Gaga and Amber Rose.

1. Bob Marley

Style is not the first thing people consider in regards to the Caribbean’s pre-eminent music legend, but Bob Marley had it in spades. Whether on a soccer field, a festival stage or in a British TV studio, Marley always exuded effortless cool. Tam caps, mostly unbuttoned button-up shirts and bell-bottom jeans were among his preferred garments, but it was his mane—and the iconic images of it—that, more than anything or anyone else, turned dreadlocks from merely a symbol of Rastafarian devotion to an ubiquitous, apolitical fashion statement. Honorable mention of course goes to Bob’s no less stylish musical partners, Peter Tosh and Bunny Wailer.