INSPIRATION: If Caribana is all about representing your true island colours, excuse me while I wave red, white and black for Mighty Sparrow (pictured above). As the undisputed calypso King of the World, Sparrow is a Trini import on par with roti, pan and the 15-year-old preacher’s daughter who wined with Akon.
“He was the top calypsonian when I was growing up as a child in Trinidad,” says Anne Marie McNamara, who was born and raised in the St. James neighbourhood (dubbed “the city that never sleeps”) of Port of Spain. She’s also my mom. “His calypsos were always controversial in the sense that there’s always sexual undertones,” she says. “He was a master at the double entendre.”
“Jean and Dinah” (1956) was Sparrow’s first massive hit. “That was the days the Americans had a [military] base in Trinidad and a lot of the local boys were pissed off that the girls were all gravitating towards the Yankees,” my mom explains, referring to the song’s social comment on the closing of the Americans’ naval base in Chaguaramas that year. Custom Legin Knits (www.leginknits.com) military-inspired beret, $40, available at Model Citizen (279 Augusta, 416-703-7625).
Of course, Jean and Dinah weren’t just any girls. “As a child you’re listening to this, [and] you think he’s just singing about two women, but when you become an adult, you realize he’s singing about two prostitutes.” Sparrow somehow makes this patriotic (and captures the tensions of a still-colonized, pre-independent nation), since there are “no more Yankees to spoil the fete” and the Trini “glamour boys” can rule once again. Vintage Trinidad & Tobago tourist shirt, stylist’s own. To find your own island-tourism t-shirt, check out your local Goodwill or go online to pick up a new Mighty Sparrow shirt ($30 at www.burdenclothing.com).

“[The calypsonians] were the town criers, singing anything that was current, whether it was a Miss Universe pageant or a mass murder scene or corrupt politicians. Whatever, they’d be singing the song.” But it’s Sparrow’s style that stands out for my mom. “He was flashy, but well-dressed.” Which is why you will do no wrong when you lime to local fetes in crisp trousers. Desperately Different by Katya Revenko (www.desperatelydifferent.com) Vinona pant, $220, available at the label’s showroom/boutique (1071 King W., ste. 108, 647-868-5579).
MODEL: SHELLINA EBRAHIM
STYLING ASSISTANT: JEANNETTE LINTON