Nearly every single day in jazz singer Billie Holiday's life was fraught with pain and suffering, but you wouldn't know that just by looking at her. Thanks to her signature red lipstick and off-the-shoulder silhouettes (often in satin and bejeweled)—along with elaborate accessories like feather boas, head wraps, and white floral headpieces—Holiday embodied sultry glamour and elegant femininity and remains one of the most influential Black style icons of the 20th century.
But underneath all of that glitz and glam was a woman who struggled with family hardship, racial inequity, and drug addiction during her all-too-short life. Born as Eleanora fa*gan on April 7, 1915, the singer endured a very difficult childhood, including sexual abuse and juvenile detention. Holiday, who took the stage name Billie Holiday from an actress she admired and her father, began performing in Harlem nightclubs as a teenager. Her distinctive voice and bold stage presence—exemplified in her performance of "Strange Fruit" at Cafe Society in 1939—left indelible marks on American music. Many credit her performance of "Strange Fruit" as one of the initial calls to action to stand up against racism, triggering the civil rights movement. Holiday also fought to integrate audiences at the clubs where she performed.
Holiday experienced true commercial success in the 1940s, recording several hit songs and records that found acclaim within the world of pop music, a rarity for a jazz singer. All the while, Lady Day (as she became known) developed an addiction to alcohol and narcotics that led to legal and financial troubles and ultimately cost her her life. In 1959, Holiday died of complications from cirrhosis; she was 44 years old.
Holiday's life is explored in the Hulu biopic United States vs. Billie Holiday, which will be released February 26, 2021. Andra Day, who plays Holiday in the film, has been nominated for a Golden Globe in the Best Actress - Motion Picture Drama category for her role. In honor of Holiday's extraordinary life and work, we're taking a look back at some of her best style moments over the years.
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1
1937
Holiday, the inimitable jazz singer who was born as Eleanora fa*gan in 1915, poses for a glamorous studio portrait bedecked in feathers and red lipstick.
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2
1939
Known for her bold style that went along with her sultry voice, Holiday was first discovered by Benny Goodman while singing in nightclubs in Harlem. Here, snowy white flowers adorning her hair and a sequined blazer are also showstoppers.
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3
1940
Holiday was born to a single mother in Baltimore, Maryland, where she lived for most of her childhood before moving to New York City. Her father, Clarence Holiday, was also in the jazz business as a guitarist and spent most of his time traveling for gigs.
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4
1942
Between 1935 and 1939, Holiday's most notable songs were recorded, thus establishing her fame. Here, she performs in New York City in a black dress embellished with a studded leather belt.
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5
1947
Here, Holiday performs at Downbeat, a jazz club in her adopted home of New York City. An eyelet dress, finished off with a statement-making oversize black bow, speaks to her larger-than-life personal style.
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6
1954
When Holiday and her mother first arrived in New York in 1928, the Great Depression was just looming around the corner. After the market's crash, Holiday was desperate for cash and auditioned as a dancer for a Harlem nightclub. When she was turned down, she then tried out as a singer, cementing her fate.
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7
1954
A floral off-the-shoulder evening gown accessorized with a diamond necklace and earrings was Holiday's choice for a performance on Valentine's Day in 1954.
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8
1957
The singer was known for inundating her music with emotion—and really made a statement with her song "Strange Fruit," penned in 1939. The song, which condemned lynchings and racism, delivered a powerful message regarding racial injustice.
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9
1957
Here, Holiday records her last album, Lady in Satin, in New York City. A simple but chic outfit of a black sweater, slicked-back ponytail, and statement earrings accentuate Holiday's striking features.
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10
1959
Holiday tragically died at the age of 44 in 1959 after a years-long battle with drug and alcohol abuse. Despite the trials of her childhood and short life, Holiday is recognized as one of the paramount jazz singers in history.
