Lexington is known for its unique eccentrics and characters, but none can surpass the notoriety and fame of "Sweet Evening Breeze", who managed to live openly as an African-American gay crossdressing male in the early-mid twentieth century.
At a time in history when the idea of being "out" was nearly unthinkable, and when most who chose crossdressing not just as a hobby but as a lifestyle had to keep it on the DL, Sweet Evening Breeze would have none of that. Instead of sneaking and slinking around, she walked brazenly down the city streets of Lexington in broad daylight. Everyone in town knew "Miss Sweets" and loved her.
And somehow, despite the rampant bigotry of the times , it worked. Sweets, thanks to her evident powerful charisma and charm, gained a huge and curious following of friends, fan, and admirers. She had friends from all walks of life, from well-to-do fellow members of the Pleasant Green Baptist Church, to more bohemian pals and acquaintances met in restrooms of the Phoenix Hotel for "Tearoom Trade".
As with many cities in those days, Lexington had a law on the books forbidding crossdressing. There’s a story often told that when Sweets and another young black drag queen were thrown in jail, they entertained the sympathetic guards with the same routines they performed in drag clubs, and ultimately swayed the judge with Sweets’ persuasive argument that the crossdressing law was unconstitutional.
Sweet Evening Breeze died on Friday, Dec. 16, 1983, at the Homestead Nursing Center. He was thought to be in his 90s and was survived by many loving friends and family. For his achievement of being himself against the odds, the Royal Sovereign Imperial Court of All Kentucky named its highest honor the James Herndon Award. Last year the Lexington Men's Chorus also named its small singing ensemble Sweet Evening Breeze in his honor as well.
Sweets' grave, bearing her birth name James Herndon, can be found in the Lexington Cemetery.