The Street Style Guide to Wearing a Headband (Without Looking Totally Juvenile)

When my editor first assigned me this story, I was aghast. The last time I wore a headband for any reason other than to hold my hair back while I washed my face or worked out was junior high.

And looking back on those photos does not make me feel warm and fuzzy inside. Instead, it summons the bad kind of nostalgia. The humiliating kind. The I-can’t-believe-anyone-let-me-leave-the-house-like-that kind.

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But after doing some street style research, I’ve discovered that headbands aren’t actually that bad. In fact, they’re pretty cute. (Not gonna lie—I actually just bought one for the first time in ages, and I’m excited to take it for a spin come autumn.)

Over the course of writing this article, I’ve gone from headband hater to full-on headband advocate. Because I’ve realized headbands can be extremely haute in the right context and with the right outfit and with the right hairstyle. You get the picture—there are a lot of moving parts. But when you nail it, you really, really nail it.

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If you’re not yet convinced (trust me, I’ve been there), flip through the below slideshow to get some sartorial inspiration. Here, how to wear a headband the right way—according to our favorite street style stars.

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