Olivia Rodrigo Gives ’90s Style a Red-Hot Update With Maile Schmidt Mules

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Olivia Rodrigo proved her love of ’90s style with her latest sleek shoe choice.

On Saturday, Rodrigo sat down with Eva Chen, Instagram’s director of fashion partnerships, for an onstage conversation at Spotify and American Express’ pop-up gallery celebrating her new album, “Guts” (released Sept. 8). For the occasion, the “Vampire” singer slipped on a pair of sleek red $380 mules from Gen Z-founded brand Maile, featuring smooth leather soles with 3.35-inch heels.

Designed by Maile Schmidt, the Kitty style was topped by two crossed V-shaped straps — one thin, one slightly wider — for a minimalist cutout effect, instantly channeling similar slip-on heels that became a hallmark of the ’90s. In a coinciding moment, Chen also wore Maile heels for the occasion, creating a unified pair with Rodrigo onstage; the fashion executive’s $350 Kourtney style featured black vegan leather uppers with 3.35-inch wedged heels, accented by curved straps topped with natural pearls.

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Rodrigo’s vintage-filled, nostalgic approach to dressing smoothly merged with Schmidt’s own brand ethos, which is similarly free-spirited and versatile.

“She’s a city girl with an island heart,” Schmidt exclusively told FN this summer at her brand’s official launch party. “She wants to be able to go from work to cocktail hour, and schlepping the New York streets in the heels. She’s fun, she’s sophisticated, but sexy — all of the feminine things that I think you can really see in the collection.”

Rodrigo opted to pair her Maile mules with an equally ’90s dress: a black knee-length slip trimmed in delicate matching lace. The piece was complete with red and pink floral embroidery — as well as whimsical strap accents — that perfectly matched the “Bad Idea Right?” singer’s footwear, creating a streamlined, coordinating moment.

The Grammy Award-winning musician’s appearance follows her return to ’90s-inspired dressing while promoting “Guts,” thanks to stylist Jared Ellner. As documented on Instagram, Ellner has virally outfitted Rodrigo in a golden crystal-coated miniskirt and cropped button-up from Todd Oldham’s spring 1995 collection, elevated with transparent slip-on mules. For a more gothic approach, he’s also dressed the singer in a black crystal mesh Versace minidress with ornate butterfly accents, all boosted by a pair of Piferi’s satin platform sandals.

Where footwear is concerned, Rodrigo often wears pairs that complement her edgy style. Black leather combat and knee-high boots by Dr. Martens, Naked Wolfe and Magda Butrym have proven to be her favorites, as well as sneakers by Vans and Converse. Her statement footwear choices often include chunky platforms or taller heels, like boots and brogues by Miu Miu, Marc Jacobs or T.U.K. On formal occasions, she can be seen in heeled styles by Giuseppe Zanotti, Nicholas Kirkwood, Sies Marjan and other high-end brands.

About the Author:

Aaron Royce is the Digital Editor for Footwear News, where he writes stories on trending news, celebrity style, collaborations and in-depth profile interviews. Prior to joining Footwear News, Aaron wrote and interned for publications including PAPER, Grazia and the Daily Front Row. He currently holds a B.S. in mass communications from Virginia Commonwealth University.

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