This piece is part of the Legacies issue, a special Pride Month series from Outward, Slate’s home for coverage of LGBTQ life, thought, and culture. Read an introduction to the issue here.
Flag-waving at Carnival is a Caribbean art form steeped in tradition, with flag-bearers sometimes referred to as “the forgotten soldiers of the steel pan world.” To win the competition at Barbados’ annual summerlong Crop Over festival, a flag-waver must make “the most spectacular use of the flag” in leading the charge of the band. In this role, as well as many others in her life, Didi Winston is usually out front and center.
Winston is the first transgender woman entertainer Barbados has ever known. A trained dancer who performed at the popular Plantation Garden Theatre Dinner Show for years, a makeup artist for the Caribbean Broadcasting Corp., and a multiwinner (20 times!) of the Winston Jordan Flag Person of the Year Award, Winston recently parlayed her movement expertise into running a fitness class. For $50, get five weeks’ worth of one-hour sessions, so you too can learn how to “wuk-up”(Bajan for a local gyrating dance move) and wave to the pulsating soca beat. Flawless legs like Winston’s are not guaranteed.