Billie Eilish Decided To Rate Her Fashion Over The Years, And Her Thoughts Range From ‘No Regrets’ To ‘Embarrassing’

Billie Eilish singing No Time To Die at 2021 Live Is Beautiful festival in Las Vegas
(Image credit: Universal Music Group / YouTube)

One especially fun part about growing up is playing with how you present yourself to the world, whether that be through one’s hair, clothing and other forms of expression. As fans have watched Billie Eilish grow up in front of the spotlight, we’ve witnessed the No Time To Die singer’s evolution as a fashion-forward artist. Ahead of Eilish heading to the Asia leg of her Happier Than Ever world tour, the young icon took a trip down memory lane to rate her bold looks over time.  

Off the heels of releasing two new songs (one referencing both Roe V. Wade and the Depp/Heard drama), Billie Eilish took to her Instagram stories to go through previous posts she shared with her followers throughout her career. (A total of 14). We’re going to start with some of Billie’s favorites and progressively get to the looks she was not as fond of. First off, fans will remember this one. During 2018’s Camp Flog Gnaw festival went more baggy than usual with this look. 

"OK, I don't need to explain this one to anyone. I was being me and this is what I wanted to wear, OK? 10/10 for having no regrets."

In the photo, a 16-year-old Billie Eilish rocked blue hair and a XL blue button up shirt, matching shorts and a ton of silver jewelry. She’s hanging out with fellow artists Tierra Whack and SZA. Eilish has received flack over the years for her fashion, but she always just does her own thing and with that pushes boundaries. Here’s another Eilish look the singer is still really happy with: 

"Cute. 10/10."

This one was featured in Billie Eilish’s 2020 music video for “Therefore I Am,” which was the second single for her now-beloved album Happier Than Ever. In the video, which she directed herself, Eilish runs around an empty mall and grabs pretzels and such while singing lyrics like “I’m not your friend” with some attitude. Here’s another one Eilish liked, but had one note for her past self: 

“Super cute, but get that shoe off the couch?! IDK what the fuck. 9/10.”

This one was taken nearly a year before the previous one, but in both instances Billie Eilish was in her black hair and green roots moment. Billie clearly loves a matching set and this one includes a muted floral print and some killer sneakers. She wore this when she received an award for Hitmaker of the Year by Variety… she just doesn’t get why her shoes were on the couch. In another look from 2019, but early in the year, Eilish shared this: 

"Reaching, but I think the fit was cooooool. 7/10."

That one, as the kids would say, went HARD. The singer who would release her first album When We All Fall Asleep, Where Do We Go? a week after that picture was posted rocked everything from a skull mask, t-shirt with a naked woman and some paisley printed paints. You wouldn’t think it would work, but she rocked it. Eilish also did a big throwback too: 

"This was my favorite outfit at the time. I wore this exact fit so many times, and loved it every time. Thought it was the coolest thing ever. Also thought my Vans were super cool. I wrote, 'Suck dicks, take shits!' on them, and I thought that was very cool. Wore these to see my childhood friends' parents in London and felt bad about it since. LMAO. 6/10."

Billie Eilish was 15 at the time, hanging out in London to chill with her friends’ family just months before going on her first tour for her Don’t Smile At Me EP. Eilish was really not a fan of herself in a red getup she went for in late 2020, saying this: 

"IDK, dude, I was grasping at straws. 5/10."

They’re not all going to be winners. That red look aside, Billie especially didn’t like this look from late 2018 in a white patterned Gucci matched set, Nike sneakers and thin sunglasses. Why? We don’t know, she just called it: 

"Embarrassing. 3/10."

These days, Billie Eilish has kept some of the sense of style we expect from her, but she no longer confines herself to one style like baggy clothes.. And that goes for music too. Remember: she even wrote the boyband music for Turning Red and went more old Hollywood for her Happier Than Ever special, streaming with a Disney+ subscription. It’s cool to see how Eilish looks back at her past certainly as we get excited for what’s in store for her future. 

Sarah El-Mahmoud
Staff Writer

Sarah El-Mahmoud has been with CinemaBlend since 2018 after graduating from Cal State Fullerton with a degree in Journalism. In college, she was the Managing Editor of the award-winning college paper, The Daily Titan, where she specialized in writing/editing long-form features, profiles and arts & entertainment coverage, including her first run-in with movie reporting, with a phone interview with Guillermo del Toro for Best Picture winner, The Shape of Water. Now she's into covering YA television and movies, and plenty of horror. Word webslinger. All her writing should be read in Sarah Connor’s Terminator 2 voice over.