10. Olivia said it herself: this outfit was a highlight of her trip to London. The pants and top combo is so fun, especially streamlined with the long, black coat. “I like, probably wore that outfit two days in a row because I was like, ‘shh, like nobody say I’m wearing it a second day but I just have to wear it again because I didn’t get pictures in it the first day,’ she recounted in her episode of Hot Ones.

9. Something about this outfit reminds me of Bratz dolls (in the best way). Her platform shoes are such a unique statement that go really well with her classic plaid mini dress. Olivia does love to layer silver necklaces, an accessorizing trick which she consistently pulls off in many of her outfits, including this one.

8. The corset craze is a thing for a reason: this top is gorgeous and sophisticated, especially paired with the French beret. I find her pants so interesting, and there’s nothing like a pop of red to tie an outfit together. Her Instagram post of this picture is captioned only with a few emojis, but Instagram’s location feature states that she was in Las Vegas at the time, and she is definitely dressed for the occasion.

7. I don’t know, I just really like her dress in this one. I want it for myself. And wearing a cute sweater with one of your own lyrics on it? Iconic. Though “Teenage Dreams” is a common phrase, her opening song “brutal” from her debut album SOUR asks, “Where’s my f***ing teenage dream?” in the second verse. At the time of her Instagram post in this outfit, SOUR had just come out on vinyl, and her little purple handbag matching SOUR’s album cover was a great way to commemorate the event.

6. One of her most memorable outfits: the pink dress from SOUR Prom. Was I the only one that noticed that one of her hair elastics must have snapped? One of the bubbles in her bubble braids was twice as long as the rest of them. In any case, her dress was so fun, especially with bright blue platform heels, that, upon inspection, match the color of one of the polka dots on her dress.

5. This outfit is literally dream-closet goals. The shiny zippers on her black pants add such a cool accent, and I just love the colors and designs on her Marc Jacobs Devon Baby Tee. Of course, the space buns are iconic as well. The background of this photo suggests she was in a photoshoot, against a backdrop the same color as that of the cover of her debut album.

4. Elle Woods who? We love to see a good Chanel matching set. The socks with the heels are a bold move for the President’s House, but it totally works. She was invited to the White House to encourage young people to get the Covid-19 Vaccine, so of course she dressed professionally. On a segment of Jimmy Kimmel Live, she said that “It was such an honor to go [to the White House], and especially to support such an important cause that I feel so passionately about, so that was amazing.”

3. Sure, we don’t see much of the rest of this outfit. But this gorgeous butterfly top was enough to bring this fit to slot number 3. She posted this photo just four days after her first big hit song “drivers license” was released, when she was very quickly beginning to gain fame and popularity. Butterflies then became one of her signature symbols, especially as her logo is composed of her initials in the shape of a butterfly, and her song “hope ur ok”’s bridge starts off with the beautiful line, “address the letters to the holes in my butterfly wings.”

2. I literally just want to own this dress. I would wear it every day. It’s such a bold color and such a flattering shape, especially on Olivia. And to wear it while holding a sledgehammer is honestly just inspiring. This outfit was worn in the music video for her song “deja vu,” which she wanted to be inspired by one of her favorite show’s, Killing Eve, though this green dress has often been compared to the green dress in the 2007 film Atonement.

1. Ok, this one is so good even fashion icon bestdressed Ashley had to recreate it, and it’s probably one of the most predictable on this list. The mini skirt, the Mimi Wade baby tee, the sunglasses, and the bright red Naked Wolfe boots that match her friend and fellow singer-songwriter Conan Gray’s purse? Showstopping. I’ve seen this paparazzi photo so many times just because of the fashion. I love it.