I’m about to start my interview when I’m interrupted.

“Let me tell you a story,” Didi says—this is how many conversations with her begin. “I was in St Joseph, the country hunty, and I figured, ‘ain’t nobody know me ’bout here’. So I go into this little rum shop and I’m dancing, wining my waist. There I am, about to do a split, and I hear, ‘wait, that’s Didi!’ Chile, I look around and this mature woman [is] looking at me and then she went [and] called about 20 people! It was drama up in there!” She throws her head back and laughs as she relates this story, and I know I am listening to a queen tell the story of her royal existence.
There are very few places one could go in Barbados where Didi Winston is anonymous. Her bigger than life personality, the bright smile, the DRAMA are unmistakable, and if you don’t know her before she walks into the room you’ll definitely know her by the time you leave. Didi says she was a precocious child, always “in the do” with an opinion on everything, but she always knew she wasn’t the same as others in her large, extended family.

“My cousins used to be looking at girls and saying they found this one attractive or sexy, or describing body parts that they liked, and I’d always shrug and say, ‘yeah, she’s pretty’. Girls never moved me in the way they did my cousins. I was always different.” Luckily, Didi says despite resistance and hurtful remarks from a few family members, she had her defenders including an aunt who’d always come to her rescue, demanding that she be left alone—a stance that even decades later is still a source of strength for her.  
Always interested in dance, Didi recalls going to see her first Kadooment parade with her grandfather.I remember seeing Kennedy, who was a flag person. I saw him and I knew that was what I wanted to do; I was so excited!”Later, she had the opportunity to meet her dance idol and the advice given will stay with her forever. “He said, ‘just do it; if you want it, just do it’. So I did.”b

Didi trained as a professional dancer with Dancing Africa and while at rehearsals, heard that legendary band leader Gwyneth Squires was in need of a flag person.

“I said ‘really?’” she dramatises. Didi won the prize for best flag person that year. Twenty years later, she has yet to relinquish that crown.When speaking about her goals, Didi said she has always known she was destined for bigger things, for better things, and she’s been keeping that in mind as she moves forward. “When I was a kid I’d always tell my friends, ‘I’m going to be on television, I’m going to be a star!’” 

Although an accomplished dancer and entertainer, Didi says she always had a love for makeup and, as a trans woman, knew she had to learn how to do things for herself.

“When we performed, at first it was…” She pauses for emphasis. “Horrendous! I knew I wanted to do my face myself so I got a makeup book and I read it from cover to cover. I was going to learn to beat my own mug.” After learning to do her own face, she says her love for makeup grew and she applied to several places for a job in the industry, but was turned down by each one. She has her suspicions about the reason for the rejection, but says that as a transwoman she pushes on, not only for herself but for the people who may come after her.  

Never one to let a little rejection derail her, Didi continued learning about makeup and was approached in the gym one day and offered a job at the Caribbean Broadcasting Corporation (CBC). “I was like, ‘that is a door, hunty and I’m kicking it in!’” Hired initially as an assistant, Didi was soon working on her own. Not long after that, she was spotted by content producers at the television station and offered a spot on a show. “…and holla! Now I’m on TV!”

Does Didi still dance? Of course she does! Every Sunday there is a cabaret performance at Ragamuffins in Second Street, Holetown, and there is still that Flag Person of the Year crown to defend. But is she now also a TV star who can do her own makeup? Of course she is! But there’s more to Didi Winston. She is also an LGBTQ activist and voice for the young people within the community.


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