There are the practical heels you wear on the regular, and then there are those extra-pretty, extra-special ones you buy in the hope of breaking them out for a momentous occasion—a birthday, a wedding, a professional milestone. Maybe they’re a bit higher, more embellished, or less “sensible” than those everyday shoes. Maybe they’re all of the above. But they occupy a beloved space in your closet, one that simply brings you joy. So why have them sit in a box? In a post-street-style world, being overdressed is no longer considered a faux-pas—whether that translates to formal pajamas for brunch, daytime tulle, or yes, bedazzled stilettos with jeans just because. Ahead, we round up 25 of those very heels—the ones so good, you can’t let them sit in the box.

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