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. 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. The shoes are crafted from sustainably sourced leather, and 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 1.75-inch 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 in heel height, 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
A 2020s version of the classic Mary Jane style.
Shop More Heeled Mary Jane Shoes We Love
Try this chunkier take on the trend.
The stacked heels and grommeted straps give off major '90s vibes.
You won't find more versatile dress shoes for under $100.
You'll want to zoom in for a better look at these black denim shoes.
We wouldn't be surprised if these shoes were named after Rodrigo herself.
Perfect for devotees of square toes and chunky heels.
This mesh design is perfect for stepping into springtime.
Try these patent-leather pumps with cuffed jeans or an A-line miniskirt.
We're partial to black, but Marc Fisher Mary Janes come in shiny silver too.
You'll want to try these on in specchio leather too.
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