Andra Day Reveals Her Favorite Red Carpet Outfits Of All Time

"If I had to sum up my style evolution, it would be a roller coaster through the decades."

by Lauren Tegtmeyer
Erik Carter

In TZR's The Looks That Made Me series, we ask celebrities to look back on the most inspirational, revolutionary, and ill-advised fashion choices they’ve made over the years. Here, TZR's January 2021 cover star Andra Day reminisces about her favorite red carpet outfits of all time.

Ask Andra Day to describe her style evolution and she'll say "it would be a roller coaster through the decades." The singer and actress always adds a retro flair to her attire for red carpet events and shared with TZR that she personally has a love for all things vintage. Day also has a penchant for hoop earrings and the colors green and red, which she frequently wears to high-profile events (and even in her photo shoot with TZR). In the video below, Day shares that this color palette often makes her "look like Christmas," but that's an aesthetic this star doesn't mind channeling — and what's better, she rocks the hues like no other.

Like any true fashionista, Day will do what it takes to make an outfit she loves work, even if it means enduring some discomfort. The cover star shares that her colorful red Roksanda dress for a Clive Davis pre-Grammy party in 2016 barely fit her, but she loved it so much that she was willing to "suffocate to keep the dress on." Aside from this memorable fashion moment, Day has more to say on some other blast-from-the-past looks, from a hot pink Chanel ensemble to a glamorous Zac Posen gown. Below, get to know the singer and actress' personal style before she makes her film debut in The United States vs. Billie Holiday on Feb. 26.

ESSENCE Black Women In Music, 2013

David Livingston/Getty Images

"That was probably one of my very first red carpets, the Black Women in Music. The dress was an actual vintage dress and the shoes I think were like Mint or something like that. I like big gaudy hoops and I like vintage styling."

Pre-Grammy Gala, 2016

Lester Cohen/WireImage

"Oh my God, that dress, I love it so much. That was for the Clive Davis pre-Grammy party. It barely fit me, too. And I was like, hell no. I was like, I will suffocate to keep this dress on."

Oscars, 2016

Jeff Kravitz/FilmMagic

"That was my first Oscars. [The dress] makes me a little emotional, actually. [The look] came together very quick. My stylist, Wouri, just sort of pulled it, and we thought we were gonna have to go through a bunch of looks, but you know, we put that one on and it just fit right away. So that was the one we went with."

Grammy Awards, 2016

Lester Cohen/WireImage

"That was my first Grammys. Everybody said I looked like Christmas. So that was actually a custom Michael Costello gown. And so I kind of put the idea together, sort of sketched it out for my stylist, and for them to design. One of my favorite colors is green, but then my other favorite color is red. So I just walk around looking like Christmas all the time."

48th NAACP Image Awards, 2017

Jesse Grant/Getty Images for NAACP Image Awards

"That was for NAACP. I actually just love things like that, where there's just sort of a hint of leg or a hint of some skin. It's just sexy, but still subtle because it's looser fitting. That [dress], I think is Victoria Hayes. We wore a lot of her stuff and still do, she's great."

LACMA Art + Film Gala, 2018

David Crotty/Patrick McMullan via Getty Images

"I love Zac Posen so much, like not just his dresses but also him. I think he's an amazing and an intuitive designer — really understands women's bodies...It was not long after I had gotten the role, Billie Holiday, and I was attending LACMA, so he sent [the dress] over really quickly and it fit perfectly. He's kind of a genius when it comes to our bodies."

Soul Train Awards Presented By BET, 2020

Leon Bennett/STA 2020/Getty Images for BET

"That [outfit] was Chanel, which I call Chanelica...I actually saw that outfit when I was in the Chanel boutique and I fell in love with it. I was like, oh my gosh, I have to have it, I have to wear it for something. One of my favorite outfits."