Shop Olivia Rodrigo’s Favorite Fancy Shoe Style at Madewell

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To suggest that Olivia Rodrigo is a fan of Mary Jane shoes would be like saying that she’s super influenced by ’90s music. At this point, it’s a well-known fact. So when we spotted these leather two-strap Madewell Mary Janes on the pop star, we knew we had to add them to our growing list of accessible Olivia Rodrigo-approved footwear.

Lately, Madewell’s shoe designs have been on point, and this pretty pair is no exception. Crafted from sustainably sourced leather and featuring the brand’s signature “Cloudlift Lite” padding makes for a feel-good pair of Mary Janes in more ways than one. We especially love the 1 3/4″ block heel for just a bit of a height boost without compromising all-day wearability. Honestly, we can’t believe they’re still in stock!

Ahead, check out Rodrigo’s latest pair of heeled Mary Janes, plus 10 more styles we think she’d be into. With variations ranging from heel height to special buckles and unique materials, this retro shoe design is anything but boring. Plus, they’ll look just as good 30 years from now when the 2020s are back in vogue—that’s one way to relive those teenage dreams.

Shop Olivia Rodrigo’s Madewell Mary-Janes

Shop More Heeled Mary-Jane Shoes We Love