Lean in a little closer. I have a secret to share: I’ve been rinsing and repeating the same pair of black Chloé ankle boots for seven years now, and I’m not planning on stopping anytime soon. They’re my emotional support boots. Facing a long day on set? The boots are packed. Need a little height boost but not feeling a heel? She’s strapping on the boots. Going on vacation? They’ll go with everything (save for a bikini). I’ve had them re-soled once or twice, but beyond that, they look and feel as good as new. They’ve practically paid for themselves at this point!

A good ankle boot is like the Swiss Army knife of fashion. A sleek leather pair will instantly dress up jeans, while a more rugged style will add edge to a frilly dress. They’re also a great transition piece between seasons, when their knee-high cousins are getting stowed away. But with so many styles to choose from, which ones will stand the test of time like my faithful Chloé pair? 

Truth be told, I didn’t anticipate them lasting as long as they did. Certain styles may feel trendy in the moment but in reality will last you several seasons. Lucky for you, I’ve lassoed a roundup of foolproof pairs to fill that ankle-boot gap in your closet (and heart).

Perveen Singh

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