How to Wear a Headband, According to Celebrities

If there’s any doubt in your mind as to how to wear a headband, now is the time to sort it out. With the the reboot of Gossip Girl on the horizon, and celebs from Jessica Alba to Zendaya wearing the accessory, the headband trend isn’t going away any time soon.

The throwback piece had a resurgence back in 2008, at the height of Blair Waldorf’s queen-bee aesthetic. It didn’t return until a decade later, thanks in part to milk braids and Prada, who sent padded nylon headbands down its spring 2019 runway. Somewhere in the middle, there was Kate Middleton and her tiara-like headbands, Chrissy Teigen’s ‘Headband of the Day’ (#HBOTD) series, and Instagram’s most-followed who made you want to buy into the middle-schooler’s starter pack.

Sure, you may look back in ten years and question your #OOTDs, but don’t let that stop you from wearing a headband now. Like scrunchies, bows, and butterfly clips, the hair accessory craze is here to stay. And we’re cool with that. Be it a padded, leather, or embellished style, a headband is an easy way to look put-together and maybe channel some Prada-girl energy while you’re at it.

But headbands are like cowboy hats in that you can’t exactly wear one timidly—you have to own it. So, rather than slipping one on as an afterthought, we looked to a few of our favorite celebs for styling tips on how to wear a headband with intention. Emma Roberts added a knotted red one to contrast her monochromatic look, while Kaia Gerber went full-on ’90s with a bandana and cropped cardi. Some break out the hair accessory whenever they need to hide a bad hair day, while others like Jessica Alba are making it part of their red carpet looks. Either way, we pored over some of their best outfits, and added look-alike shopping options. Here are nine ways to wear a headband in 2020.

Chrissy Teigen

Emma McIntyre / Getty Images

You’ll never get to hold hands with John Legend, but you can fall in love with the way Chrissy Teigen’s Jennifer Behr headband levels-up up your look. Layer your dress over jeans, and swap the Alexandre Birman heels for boots so you can wear this weekend brunch outfit even in the heart of winter.

Jennifer Behr Triple Rosette Hammered Silk Headband

Moda Operandi


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Classic Straight Jeans: Selvedge Edition



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Loveshackfancy Floral Ruffle Cotton Dress



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Anthropologie Knotted Headband



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Bella Hadid

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