A History of Style: Fashion Inspired by Billie Holiday

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Billie Holiday

When you think of a fashion icon from the past, who is the first person that comes to mind? Marilyn Monroe? Audrey Hepburn? Edie Sedgwick, perhaps? While all three of those women have enviable styles that we absolutely love, there are so many other fashionable women that have graced the history pages.

This bi-weekly column focuses on just that: unexpected and out-of-the-box fashion icons from the past. We feature women who are not only made an impact, but have a distinct signature style that we can still draw inspiration from today.

Last time, we took a closer look at Amelia Earhart’s menswear-inspired style, and now we’ll be discussing the influential jazz singer Billie Holiday. Read on to learn more about her life and unique style, then check out some outfits ideas to help you channel her look for yourself:


5 Facts About Billie

  • Billie was born Eleanora Fagan Gough on April 7, 1915 in Philadelphia, Pennsylvania. She later adopted the stage name ‘Billie Holiday’ after her admiration for an actress named Billie Dove.
  • When she was just 17 years old, Billie began singing at jazz clubs in New York City. She was discovered by a music producer in 1933. By the time she was 18, she had already cut her first album.
  • Billie was given the nickname Lady Day by her friend and musical partner Lester Young, which stuck with her throughout her life.
  • Billie was known for her unique, distinctive singing voice and many of the songs she recorded became jazz standards. Some of her more famous songs include “Strange Fruit”, “Easy Living”“God Bless the Child” and “Fine and Mellow”.
  • Unfortunately, Billie had struggled with drinking and drug problems for many years, which ultimately resulted in her death on July 17, 1959 at the young age of 44.

Billie’s Style 101

  • Elaborate Hair Accessories. Billie was often photographed wearing her signature accessory: beautiful flowers which she pinned in her hair. For an authentic Billie-inspired look, adorn your hair with fresh flowers or look for a floral hair clip or headband.
  • Statement Jewelry. Never one to blend in with a crowd, Billie liked to wear lots of gorgeous, statement-making jewelry. She wore chandelier earrings, cocktail rings and strands of pearls for a lounge-like vibe which can easily be mimicked today.
  • Fancy Frocks. Even when she wasn’t performing, Billie always accentuated her curves with gorgeous, body-skimming dresses. Printed, lacy or bejeweled, Billie looked amazing in every dress she wore. Channel her style for yourself by wearing a fancy dress during the day or by rocking a show-stopping cocktail dress for a formal party or event.
  • Luxe Details. Whether she wore an oversized bow, a fur coat or a sequin-encrusted sweater, Billie knew how to make a statement with her wardrobe. She always wore pieces with that extra dose of pizzazz, which made her style anything but average.

Outfits for Inspiration

Lady Sings the Blues

Billie Holiday Outfit1

Product Info: Hair Clip- Nordstrom, Dress- Warehouse, Necklace- Wet Seal, Ring- H&M, Watch- 1928, Flats- H&M

Autumn in New York

Billie Holiday Outfit 2

Product Info: Head Wrap- ASOS, Sweater- Oasis, Earrings- ASOS, Flats- H&M, Pants- Forever 21, Ring- ASOS

I’m Painting the Town Red

Billie Holiday Outfit 3

Product Info: Coat- H&M, Dress- ModCloth, Hair Clip- Ruche, Pumps- ModCloth, Clutch- Monsoon, Earrings- Macy’s

What do you think?

Do you find Billie’s style inspiring? What do you think of her look? Would you wear any of these outfits? Which Billie Holiday song is your favorite? Let me know what you think by leaving a comment below!

10 thoughts on “A History of Style: Fashion Inspired by Billie Holiday”

  1. Billie Holiday has the most magical voice, and I am so glad to see CF picked up on her style as well! I’ve never seen anyone do a fashion spread with her as inspiration, so bravo!

  2. I love everything fashion! Especially the 20-50’s eras. Please continue to bring us fashion from the past!
    Valeria High PlusModel

  3. Really love her style. Doubt I look as cool but it was interesting to see that I was actually emulating her style all long. This era of fashion is one of my favs in general though

  4. I LOVE the shoes in #2, does anyone know where I could get a similar pair? I’m not from Great Britain so I can’t order the ones from H&M GB. =[

  5. I love the second outfit, the head band reminds me of something Billie Holiday would have worn, and it resembles classic style from the 1920s.

  6. love outfit 2. i seriously want that headband now–and those earrings, and that sweater. would probably substitute leggings, because i’ve been spending all my time in the library and leggings are so comfy, and boots, because it is seriously cold, but i love the look.

  7. fav outfit is #3 love the pants & pair w a oversized sweater makes it cozy & perfect for colder weather. also like the idea of long sleeved sweater dress even tho i wudn’t wear that 1 (dresses tend not to look gud on me) but u did gr8 job bringing out the blues part of that. also love the red dress but be practical, wear exactly wud the average college girl wear that? neway gr8 post thank you


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