The Enduring Legacy of Billie Holiday’s Exquisite Style

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What would you wear to the police station if you were arrested in San Francisco in 1949? If you were the iconic singer Billie Holiday, you would swath yourself in a vast mink coat with enormous sleeves, wrap your head in a perfect turban, and view the entire degrading affair through a pair of chic dark glasses.

Holiday was born 102 years ago April 8th to a very young mother. By all accounts, she had an extremely rough childhood. By the time she was a young teenager, she was developing the utterly distinctive voice that would transform American music—as Frank Sinatra told Ebony magazine in 1958, “With few exceptions, every major pop singer in the U.S. during her generation has been touched in some way by her genius.”

Holiday served jail time for drug charges, but heroin was only one of the challenges she faced. She was also the victim of unrelenting racial prejudice. “You can be up to your boobies in white satin, with gardenias in your hair, and no sugar cane for miles, but you can still be working on a plantation,” she once declared, describing life on the segregated road.

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But oh that satin, those gardenias! Holiday’s incredible fashion sense—her off-the-shoulder dresses; her bejeweled frocks; her head wraps; the big glittering rings, bracelets, and earrings she favored—inspires us not in spite of, but because of, her fierce resistance. But, of course, it didn’t matter how splendid you looked in your silk and your pearls—you were still barred from many hotels and restaurants as you toured the South with the biggest bands in the country, you would still be asked to leave a bandstand rather than share it with white performers, and you would still be instructed to use the service elevator at the Lincoln Hotel, right here in New York City, instead of the passenger lift.

When Holiday sang “Strange Fruit” at Café Society in Sheridan Square (The lyrics describe a lynching, and she said it always reminded her of her father, who she believed died because he was denied proper medical attention.), the lights in the cabaret dimmed, leaving only a spotlight on her face. At the end of the song, the room went dark. By the time the lights came back on, Holiday, in her sleek gown with a gardenia planted firmly on her exquisite head, had already vanished from the stage.

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We will never sit in that audience at Café Society and be in her presence, but we can pay homage to Lady Day and honor her courage and her inimitable style on what would have been her 102nd birthday.

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