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On Oct. 5, 1958, Billie Holiday took the stage at the inaugural Monterey Jazz Festival. Then America’s preeminent jazz singer, she closed the event with an effortlessly sophisticated 11-song set that mirrored the image she had carefully crafted for herself over the years: makeup perfectly applied, ebony hair pulled back into her trademark ponytail. Her shimmering strapless evening gown was patterned with stars and complemented by dangling earrings and a mink stole. She was the picture of stylish elegance.

It was no accident. During a career that began in the early 1930s and lasted until her death at 44 in 1959, Holiday honed a look that counteracted the prevailing sentiments of a culture defined by Jim Crow. She deflected racial animosity by countering the negative stereotypes of African Americans embodied by tropes such as “Amos ’n’ Andy” and Aunt Jemima. Holiday was doing much more than making music, says Scherrie Payne, who sang with the Supremes in the mid-’70s. “She was making a statement for the Black woman.”

That statement was bold and unambiguous, and it continues to reverberate through popular music. “Billie Holiday is one of the great fashion icons,” says style guru Tim Gunn, host of “<a href="https://urldefense.com/v3/__https:/www.amazon.com/gp/video/detail/B0B5HP8KC5/ref=atv_dp_season_select_s3__;!!M9LbjjnYNg9jBDflsQ!F8BifDSPVlyq1jclWHmDYzO0ZzHnWf8QslZJVA24E54PV81OXGzL1TSIDJ5kMaFpbiHjx0Gf7OQkMjY_lJO_FbrvaHeVGw$" target=_blank>Making the Cut</a>.” “She embodied a grand elegance [with] a profound edge to it. What she exuded said everything. It said, ‘I’m a woman who struggled, but I have great confidence and I want you to know I’m here.’ Her stage presence was charismatic, and the clothes said it all. She was a trailblazer.”

As her fame grew, Holiday would face more than the prejudices of the day — federal and local government agencies were intent on diminishing her stature as a public figure. The persona she built was a bulwark against such efforts. The image was of a dignified, elegant “lady” — a fact underscored by her nickname, Lady Day. She even included the word in two of her best-known album titles, “Lady Sings the Blues” and “Lady in Satin.”

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Her interest in fashion began in an unlikely place. Growing up in Baltimore’s Fells Point, she was often cared for by family and friends while her mother accepted long-term domestic jobs in other cities. Around age 12, Holiday began spending time at two neighborhood bordellos, one owned by Alice Dean, the other by Ethel Moore, and became captivated by the women’s wardrobes — the furs, the jewelry, the evening dresses. “Her mentors … were madams,” wrote journalist Linda Kuehl, who did extensive research for a Holiday biography that was never completed. “In their houses she began … singing the pop tunes of the day.” Holiday later used the trappings of that world — the music, alcohol and drugs as well as the gowns and minks — to create a lasting artistic persona.

During the 1930s, when she played Harlem nightclubs and toured with Count Basie and Artie Shaw, Holiday’s fashion sense continued to develop. At first, she wore simple fitted day dresses set off with accessories such as jackets or belts. Her style had become more distinctive by the time reporter Lillian Johnson observed in a 1937 Baltimore Afro-American profile: “[H]er street clothes for the day consisted of a soft fierce sports coat in dark gray with a blue fox collar, a gray skirt, and a short woolen jacket of brick. For her stage appearance, she donned a black chiffon, fitted evening gown with a black satin underslip trimmed with rhinestones at the neck. … She wore three white gardenias [in her hair]” — a hallmark of her stage appearance for years.

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“Like most stylish women,” says Coty Award-winning designer Jeffrey Banks, “like Diana Vreeland and Coco Chanel, Billie Holiday had her signatures — the flower behind her ear, deep red lipstick, later on the ponytail — because she wanted people to remember her look.”

From 1939 to 1941, Holiday headlined at Café Society, the iconoclastic Greenwich Village nightclub known for integrating both its talent and its audience. Her wardrobe evolved considerably during this period as a result of a long-term affair she had with arts patron Louise Crane, whose family’s business, Crane &amp; Co., counted among its clients the U.S. government, since Crane supplied the Treasury Department with the paper used to print currency.

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“[Louise] was good to Billie,” says Irene Wilson Kitchens, Holiday’s friend and first wife of pianist Teddy Wilson. “She took her to Bonwit Teller. That’s where Billie got her first fox. [Billie] was so childish about it, like a big kid. ‘Renie,’ she said, ‘Look what I got. I got a silver fox.’ That was the beginning of Billie getting really nice things to wear, the lovely evening gowns and things. Before it was over, Billie was the most glamorous thing there was. No one in the business looked better than [she did], and [Louise]” — for whom money was never an issue — “had a lot to do with it.”

While her look was deeply personal, in historical context it was also intensely political. “She had an eclecticism to her style, much like her musical predecessor Josephine Baker,” says Darnell-Jamal Lisby, a fashion historian at the <a href="https://www.clevelandart.org/" target=_blank>Cleveland Museum of Art</a>. “Holiday was also three or four generations out of emancipation [her great-grandmother was, in fact, an enslaved person], when African Americans were finding a way to be seen as equals. Holiday was reclaiming her Blackness, her womanhood.”

In the mid-1940s, Holiday developed a drug addiction and, in 1947 and 1948, served almost a year in prison for narcotics possession. After her release, maintaining her image of class and refinement was more important than ever, as she was routinely labeled a criminal in the press. In her comeback concert at Carnegie Hall, held days after her prison release, she appeared in, according to costume designer Bobby Goodrich, “an iconic white dress with a bodice of sequined fabric and a trim of pleated chiffon ruffle and a bottom half of the dress featuring layers of chiffon.” A white choker necklace and her hair pulled on top of her head into a ball finished the look, which was calculated for its effect. As Banks observes, “Billie Holiday used clothing to say, ‘I may have just been let out of prison, but I’m still viable.’”

While authorities pursued her over the next decade, Holiday’s public image continued to counteract the often-negative depictions of her in the media. She was arrested in 1949 in San Francisco, but in the press coverage of her booking — for which she donned glamorous sunglasses and an $18,000 full-length mink — she looked like a movie star. So important was her role as a fashion influencer that when she died, coverage of her funeral invariably included a description of her burial outfit: a rose Chantilly lace gown with long sleeves, pink gloves, a five-strand pearl necklace around her neck and a halo of white gardenias in her hair. Even in death, Holiday was the epitome of class and grace.

Only after she died did the staying power of her image become apparent. When Aretha Franklin hit the music scene in 1961 — Holiday knew her so well in the late 1950s that she had Franklin’s telephone number in her address book — she echoed the jazz legend’s image. Franklin often appeared in chic gowns, some of which featured the embroidered patterns Holiday favored. Jazz singer Nancy Wilson was similarly inspired by Holiday to create her own refined look, which was so acclaimed that two of her gowns now hang in the Smithsonian Institution. As Gunn says, “In fashion history, something is always begetting something else.”

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Holiday’s most consequential influence was arguably on the <a href="https://www.motownrecords.com/" target=_blank>Motown</a> look. During the 1960s, under the watchful eye of founder Berry Gordy, the presentation of his Motown artists — with the men such as Smokey Robinson flawlessly groomed and dressed in tailored suits and the women such as Diana Ross clad in sleek dresses accented by coifed hairstyles — had a profound effect on the way the African American community was perceived by the general public.

“Gordy’s ambition was to make Black music respectable and salable to a White audience,” says Peter Benjaminson, author of “<a href="https://urldefense.com/v3/__https:/www.amazon.com/Story-Motown-Peter-Benjaminson/dp/1947856235__;!!M9LbjjnYNg9jBDflsQ!F8BifDSPVlyq1jclWHmDYzO0ZzHnWf8QslZJVA24E54PV81OXGzL1TSIDJ5kMaFpbiHjx0Gf7OQkMjY_lJO_FbrBSDs9KQ$" target=_blank>The Story of Motown</a>.” “He wanted the look to be stylish and attractive. Billie Holiday was Motown’s immediate predecessor. It’s obvious she was an influence, and Gordy made that clear with his first movie: ‘Lady Sings the Blues.’” Payne believes “Berry wanted to create a classy look, and Billie Holiday was classy. She was the lady in satin. She was regal.”

It was her music that allowed Holiday to enter the pantheon of indelible American artists, but she used her platform to forge an image that made an impact of its own. “It’s symbiotic,” says Valerie Steele, director and chief curator of the <a href="https://www.fitnyc.edu/" target=_blank>Fashion Institute of Technology</a>. “You can’t separate her voice from her appearance. You see her and you hear the music as well.” And her influence continues. Lisby points to Beyoncé’s look at the 2007 Grammy Awards ceremony, “when she wore a ’20s-inspired dress and a gardenia in her hair. And there are more artists who have been influenced by Billie: Sade, early Whitney Houston, Mariah Carey — they all take a page out of Billie’s playbook.”

Ultimately, Holiday crafted what Nichelle Gainer, author of “Vintage Black Glamour,” calls “a classic, sleek timeless look someone could wear today.” And that, after all, is the aspiration of any fashion designer: a timeless creation. Holiday may have intended her look to ward off the hostile forces in her life, but in the end she conceived a style as eternal as her music.

A previous version of this article stated that Billie Holiday's grandmother was an enslaved person. In fact, her great-grandmother was enslaved. The article has been corrected. 

Paul Alexander is the author of “<a href="https://www.amazon.com/Bitter-Crop-Heartache-Triumph-Holidays/dp/0593315901/ref=tmm_hrd_swatch_0?_encoding=UTF8&qid=&sr=" target=_blank>Bitter Crop: The Heartache and Triumph of Billie Holiday’s Last Year</a>,” which was published last month. He teaches at Hunter College.

Paul Alexander

Billie Holiday’s signature style was more than a fashion statement

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Billie Holiday’s gowns and gardenias were an assertion of dignity

The jazz legend’s signature style was a rebuke to both the prejudices of the day and the negative press generated by her arrests