STYLE EVOLUTION
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Andra Day’s Best Red Carpet Looks Prove She Can Channel Any Era

Photo by Jon Kopaloff/FilmMagic

Andra Day has a knack for interpreting several types of glamour on the red carpet. Often, the singer and actress seems like she’s stepped directly out of the ‘60s, but she can also channel old-school Hollywood—as evidenced by her recent run of appearances to promote (and collect awards for) her film The United States vs. Billie Holiday. Clearly, her looks are thought out from head-to-toe, because often the glam stems not just from her clothes, but the hairstyle and accessories she’s chosen to match. Few have figured out how to feature flowers on the red carpet quite like Day. Sometimes they’re festooned in her hair—other times, they’re a simple accessory.

The red carpets she’s attended also tell the story of her career. She first came to prominence with her 2016 debut album Cheers to the Fall, which was nominated for several music awards. More recently, she received an Oscar nod for her performance as Billie Holiday. And in between, Day is known to show up at events to support the causes she believes in. Here, a look back at Day’s best red carpet moments.

2021: The Academy Awards

Andra Day wore a custom Vera Wang Haute metallic gold gown, in honor of Billie Holiday, to celebrate her Best Actress nomination for her role in The United States vs. Billie Holiday at the 2021 Oscars.

2021: Critics’ Choice Awards
Photo by Myriam Santos via Getty Images

The Critics’ Choice Awards were a Zoomed-in affair this year—so even as a nominee, Day decided to wear pants. They were part of a custom Prada outfit, however, that gave traditional “gown” from the waist up, but still made for a striking silhouette altogether.

2021: Golden Globes
Photo by Stefanie Keenan/Getty Images for CHANEL

Day took home the award for Best Actress in a Musical or Comedy at the 2021 Golden Globes wearing Chanel Haute Couture.

2020: The Soul Train Awards

Attending the Soul Train Awards, Day channeled the ‘60s in a Chanel two-piece set.

2018: The Academy Awards
Photo by Jeff Kravitz/FilmMagic

At the 2018 Academy Awards, Day had fun with volume and florals in a Zac Posen gown.

2019: The Grammy Awards
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At the 2019 Grammy awards, Day channeled a vintage vibe wearing Cheng-Huai Chuang.

2018: Rock & Roll Hall of Fame Induction Ceremony
Photo by Jeff Kravitz/FilmMagic

Performing at the 2018 Rock & Roll Hall of Fame Induction Ceremony, Day again went with a statement Victoria Heyes coat dress.

2018: Grammy Awards
Photo by Jamie McCarthy/Getty Images

Here, Day paired a Victoria Heyes coat dress with a simple statement flower.

2018: NAACP Image Awards
Photo by Paras Griffin/Getty Images for NAACP

Day chose a sparkling Giorgio Armani number here.

2017: ACLU SoCal Hosts Annual Bill of Rights Dinner
Photo by Matt Winkelmeyer/Getty Images

The all-black palette was simple, but Day still made a statement.

2017: UrbanFilm Festival
Photo by Mychal Watts/WireImage

Day went for a colorful vibe at the 2017 event.

2017: Grammy Awards
Photo by Jon Kopaloff/FilmMagic

For the 2017 Grammy Awards, Day pulled vintage Christian Dior, which she offset with blossoms in her hair.

2017: NAACP Image Awards
Photo by Jason LaVeris/FilmMagic

Day went for a bold pattern in blue and some statement shades.

2016: Pandora Event
Photo by Noam Galai/Getty Images for Pandora

At an event for Pandora jewelry, Day went back to the ‘20s for inspiration.

2016: Kennedy Center Honors
Photo by Paul Morigi/WireImage

At the Kennedy Center Honors, Day made a robe feel red carpet-appropriate.

2016: Academy Awards
Photo by Jeff Kravitz/FilmMagic

Years before she would be nominated herself, Day wore a pale yellow gown to the 2016 Oscars.

2016: Marc Jacobs Show
Photo by Dimitrios Kambouris/Getty Images for Marc Jacobs

Marc Jacobs was an early admirer of Day’s style-star potential, inviting her to sit front row at a 2016 show.

2013: John Varvatos 10th Annual Stuart House Benefit
Photo by Frederick M. Brown/Getty Images

In 2013, Day kept it simple in a scarlet jumpsuit at a John Varvatos charity event.

2013: ESSENCE Black Women In Music Event
Photo by David Livingston/Getty Images

Even during her earliest red carpet appearances, it was apparent Day had a taste for channeling vintage vibes.