Olivia Rodrigo is sticking to her dainty, vintage vibe as she promotes her new album, “You Seem Pretty Sad for a Girl So in Love.” The singer was spotted out and about during the week of the project’s release as she headed to appear on “Jimmy Kimmel Live!” on Thursday.

Olivia Rodrigo

Rodrigo performed “the cure” from the new album on the show, but ahead of the late-night show taping, she wore another Y2K-inspired look that she topped off with Miu Miu heels. The singer opted for a vintage pair of Miu Miu’s Leather Plaid Print Slingback Pumps. The pumps feature a distinct floral-print inner lining.

The shoes feature a round toe, with a slight opening at the toes, creating a peep-toe pump design. The shoes were completed with a leather trim around the top line and were decorated with a feminine bow detail on the toe. The heels stood tall on a sculpted, curved block heel measuring around three inches, which added just enough lift.

LOS ANGELES, CA - JUNE 10: Olivia Rodrigo is seen on June 10, 2026 in Los Angeles, California.  (Photo by PG/Bauer-Griffin/GC Images)

A close-up of the shoes.

GC Images

The shoes tied the whole look together, which was heavily influenced by what people wore in the early 2000s. She paired a Mimi Wade Ciggie Lace Trimmed Baby T in white, which showed just a glimpse of her midriff. She paired the T-shirt with ultra-low-rise Bluey Denim Vintage Edwin Jeans in a medium wash with a slightly flared leg that complemented the shoes. She accessorized the look with a Fendi Pink Sequin Baguette.

“You Seem Pretty Sad for a Girl So in Love” is Rodrigo’s third studio album and drops this Friday. The album was preceded by two singles, “Drop Dead” and “The Cure,” which she followed with two music videos. Rodrigo is known for wearing lace-up combat boots by Dr. Martens when she is on stage but she has leaned into more delicate for this new era.