Olivia Rodrigo's Best Street Style!

At just 20 years old, Olivia Rodrigo has become one of the biggest and most beloved young artists in the music industry. When she’s not busy owning the red carpet or writing our next favorite song in the studio, she can be seen displaying unique street style looks. In the past few years, Rodrigo has established herself as an innovative fashion icon with Y2K influence, emulating early-2000s trend-setters such as Avril Lavigne, Christina Aguilera, and Paris Hilton. Her style is quintessential Gen-Z: alternative, nostalgic, pop princess-y, and always playful and distinctive. She’s known for loving a pair of Doc Martens or platform boots, rocking a fun mini-skirt, and always accessorizing with a pair of cute sunglasses. Whether she’s shopping with friends or traveling the world, Rodrigo is defining the fashion zeitgeist of her generation. 

1. Head-to-Toe Early-Aughts

As we will see in all of these outfits, Rodrigo loves to play with textures, patterns, and colors. From top to bottom, this Y2K dream made her look like the main character that day as she left after an appearance on “Jimmy Kimmel Live!” in Los Angeles. This look features a shiny satin olive green midi-skirt from NoDress 67, and the touches of green carry into the hair bows in her braids as well as in her custom-made plaid corset top from Pristine. Along with her signature Doc Martens, she’s wearing an eccentric charm necklace from Marland Backus and a handbag from Marc Jacobs’s Heaven collection. 

2. London is Lovely 

This outfit from a day in London showcases more of her fanciful patterns and texture mixing. From the statement coat to the multi-colored pants, she is giving off effortless cool girl. The jeans are vintage '90s Jean Paul Gaultier Basquiat denim, the baby tee is from Marc Jacobs’s Heaven collection, the orange-tinted rectangular glasses are from Gucci, and for shoes, she is wearing a classic pair of Converse One Star sneakers. Last but certainly not least, the coat that makes us want to jump on a plane to somewhere chilly immediately: a black knee-length coat from Saks Potts. 

3. Beaded in the Big Apple

In 2021, a superstar was born, and that same year, this superstar had many major Bucket List moments, like making her "SNL" debut! Before she took the stage in some killer outfits, she made sure to still stun on the streets of New York when arriving at rehearsals. Rodrigo sported a checkered black and green beaded skirt and top from Erika Maish. She paired this set with a casual leather jacket and a pair of knee-high lace-up boots. 

4. These Boots Are Made for Walkin’

Nobody has a better shoe game than Rodrigo, and when these photos dropped, she left fans all over the internet with their jaws on the floor. I mean, can we hear a little commotion for the boots?! While shopping with friend Conan Gray, she wore Mayhem Red Patent Platform Boots by Naked Wolfe, a low-waisted gray mini-skirt with pleats from NoDress 67, a Marilyn baby tee from Mimi Wade, and a pair of Alyssa Sunglasses from APERÇU Eyewear. 

5. A European Summer

I’m pretty sure Rodrigo wrote “jealousy, jealousy” about all of us looking at her travel outfits, and this ensemble that she donned during a European excursion is one of our underrated favorites! While performing on tour for her debut album SOUR, she still dressed to impress during her outings around different cities. Pictured in front of Duomo di Milano in Milan, Italy, she wore a pair of James Dean graphic pants sourced from Tired Thrift, a chic black tube top with a white ribbon, a pair of platform shoes, and her staple – a pair of rectangle sunglasses. 

6. Crochet All Day

And we’re back in London! Rodrigo loves to play around with unconventional crochet pieces and knitwear, and she’s nailed down the perfect way to style these unique garments. She’s completely mastered the art of balancing punk and grunge with girly and delicate, and she does so here by combining soft textures with hard patterns and shapes. Posed in front of red telephone boxes, she wore a custom sweater and the Scrap Beanie from UR GF. She paired these crochet pieces with a black skirt from Edikted, fishnets, fingerless gloves, and a pair of black platform boots. 

7. '90s It-Girl

If we increased the grain level on this photo, we could argue that this is simply a shot of an iconic '90s star out and about in New York. Before performing at the legendary Radio City Music Hall, she made her way through the crowd with mixed patterns and a sleek bun in one of her go-to brands, Marc Jacobs. The blue sweater is the “Kissers Vest” from Marc Jacobs’s Heaven collection, and she styled it with a plaid skirt, a pair of Creepers shoes, and turquoise-tinted sunglasses. We’re obsessed!!