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The 15 Most Comfortable Mary Jane Shoes You’ll Wear on Repeat
Jan 23, 2025
Mary Jane shoes have taken the footwear world by storm, and every brand has its own interpretation of the ladylike shoe. From Sézane, Kate Spade, and Rothy’s to Dr. Martens and Christian Louboutin, there’s truly something for every kind of style at every budget. With that in mind, I’ve tried on dozens of Mary Jane styles over the last year and searched high and low on the internet for reviews to make sure you have the most comfortable options available. So, whether you’re looking for a chic everyday shoe or a statement piece for a special occasion, the wide selection of Mary Janes ahead will never have you compromising comfort for style.

Best Insole for Foot Health

Easiest to Wear

Best Insole for Foot Health

Vivaia Pointed-Toe Mary-Jane Flat

Vivaia’s “comfort heels” pretty much broke the internet through targeted ads (sorry, not sorry; if you haven’t seen them yet—you’re going to want to). This modern take on classic ballet flats features the same shock-absorbing midsole and contoured footbed that makes the brand’s heels so comfy. You get sneaker-like comfort and an anti-slip grip in a sophisticated style.
Colors: 12 options
Sizes: 5-11
Material: Antimicrobial knit
Customer review: “Love the shoes, they fit perfectly, look great, and are so light and comfortable.”
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