Olivia Rodrigo Is Officially in a New Style Era

This one is for all of you “20-something-year-old teenagers” out there.

Preppy, edgy, cool and youthful — those are just a few descriptors that come to mind when it comes to the Olivia Rodrigo style evolution while promoting her newly released sophomore album, Guts.

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Since her first major acting gig at 12 years old, the now 20-year-old actress and singer is proving that she’s come a long way from her Disney Channel days, both with her most outfits and mature music. Coming off the heels of her wildly successful debut album Sour, Rodrigo’s Guts has steadily climbed the charts since its release on September 8.

Just look to the thousands of “20-year-old teenage” fans on social media who have been applauding Rodrigo for her honest, raw lyricism as well as the edgy and nostalgic sound of the album. Some have even noted how the record could have easily been the soundtrack to a number of classic teenage movies from the late ’90s and early 2000s (think 10 Things I Hate About You and Freaky Friday).

And it seems that Rodrigo has fully embraced her latest era by taking on a renewed main character energy, one that includes the daring, pop-punk elements of her new sound mixed with the quintessential cool-girl vibe that she’s curated over the years. Lately, Rodrigo’s been pulling off her gutsy new style by opting for some Y2K graphic tees, a series of cute mini-skirts and the classically preppy socks with loafers and Mary Janes look.

As one of Gen Z’s biggest celebrities, Rodrigo’s latest sartorial adventure is solidifying both her pop star and fashion icon status — and it seems like she’s only just getting started.

Check out some of Olivia Rodrigo’s best style moments from her Guts era (so far) below.

Pulling from the fashion archives

While celebrating her new album’s release, Rodrigo showed that she not only knows what works for her style-wise, but that she’s also well-versed in fashion history with this archival look from Todd Oldham’s spring 1995 collection. By combining the white satin cropped button-down that supermodel Shalom Harlow once sported with the glittery gold mini-skirt that fellow super Amber Valletta wore during the duo’s iconic 1995 runway moment, Rodrigo paid homage to one of the most exciting moments in ’90s fashion history while staying true to her youthful and daring style as of late.

The statement graphic T-shirt

The graphic tee and mini-skirt combo was one of Rodrigo’s go-to outfits this past summer and we’re not mad at it. While out and about in London ahead of the release of Guts, the singer wore a simple grey mini with a vintage-inspired T-shirt featuring rock star Pat Benatar. She completed the look with some very ’90s accessories, including several silver rings, her all-black shades and black Mary Janes with white socks.

A modern take on mod fashion

In a slight deviation from her usual darker, more overtly grunge style, Rodrigo sported this all-white look in London this summer. In a fuzzy mini-dress from Patou (that actually features a small triangle cutout in the front, which Rodrigo opted to hide by cleverly wearing the dress backwards) and knee-high white patent leather boots, Rodrigo seemed to be taking a break from her usual ’90s-inspired style for a more 1960s-themed look. But since mod style was actually known to be at the forefront of “risky” fashion at the time, Rodrigo may have been sticking to her edgy style persona with this look after all.

A virtual pop-punk look

To promote her album by hosting a virtual meet and greet inside of a Target (which has since gone viral for it’s slightly dystopian tone), Rodrigo looked the part of a futuristic pop-punk superstar. The singer wore a black tank top with a plaid red skirt (a fashion favourite for Rodrigo) and a matching red lip. What really tied the outfit together though were the knee-high black patent leather heeled boots that the pop star used to complete the look.

Floral with a twist

For a Guts pop-up event in NYC, Rodrigo wore a classic little black dress with a bold twist in a vintage Betsey Johnson number adorned with flowers. For an extra pop of colour, the singer matched her red strappy heels and signature red lip back to the frock’s rosettes.