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Strategist writer Erin Schwartz describes them as peak Ivy League, Walcott by Vampire Weekend, tennis-lessons-on-the-weekends loafers with an aura powerful enough that it turns anything I wear into prep cosplay. And when we started reporting for this story, the pair was mentioned again by Biz Lindsay, head of corporate communications at Harrys Razors, who named the Weejuns her favorite flats, hands down

So after several months of intense debate, we tally the votes, collate the anecdotal evidence, and emerge with a list of what we believe to be the absolute best of the category right now, from the tried-and-true stalwarts to the modern disruptors, the affordable beaters to the wildly expensive (but wildly worth-it) designer riffs

JIL SANDER Lune Leather Knee Boots Sculpted heels are one of the biggest footwear trends of 2026

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