Pop Style: Sheldon Shepherd

Interview by Tami Tsansai
Photos by Martei Korley

Welcome to LargeUp’s new street style feature, Pop Style. Every other Friday, we’ll be talking sartorial shop with the most impeccably dressed men and women of the Caribbean and the diaspora, from familiar faces to everyday people pon di corner. Along the way we intend to show the world what we’ve long held true—no one’s got style and swagger quite like the islands.

Sheldon Shepherd
Dub poet (with the group No-Maddz), and actor
Spotted in: Havendale, Kingston, Jamaica

LargeUp: You seem to have a knack for handling kittens, are you a cat person?

Sheldon Shepherd: Yes. I am an animal person and I also think every home should have a cat or two.

LU: Can you describe what you’re wearing?

SS: The pants and shirt I actually designed myself. The jacket is vintage, bought it in Seoul, Korea. Ray Ban wayfarer shades, a straw fedora and Jah Laddins.

LU: Do you wear these ‘Jah Laddin’ shoes everywhere? How did you come to adopt these shoes as part of your look?

SS: I only wear them on stage when I am performing my genie act. The shoes were divine intervention.

LU: Is this a performance outfit? Do you dress differently for your shows than you do on your down time?

SS: I am always performing… all the world’s a stage.

LU: How has your style has evolved from your earlier years to now?

SS: In the early days, I used to wear big stuff, now I wear my correct size… “couture”.

LU: Do you enjoy fashion, or did it just come with being in the spotlight?

SS: I always played dress-up as a child. I would draw my own designs, cut them out and fit them unto action figures.

LU: Your style appears to be an amalgam of ‘gentlemanly sartorial elegance’ and ‘rude bwoy,’ but while there are others who dress similarly, you manage to make it feel original. What’s your secret?

SS: The secret is really the man in the clothes, not the clothes on the man.

LU: What is your favorite thing to wear?

SS: Hahaha… nothing!