How to Wear a Headband If You’re Not Blair Waldorf

How to Wear a Headband If You’re Not Blair Waldorf

BY ANNA J. STAINSBY                                           ONLINE DIRECTOR

When I put a headband on for our last 1920s themed Speakeasy I figured it would be a one-time thing. For one, they tend to hurt my skull quite a great deal. But the crux of my issue with headbands is that I cannot help but feel preppy and/or childish with one on if it’s not for the purpose of a costume.

That said, two days later, I somehow found myself on Amazon, clicking on a thumbnail of a black headband going for $6.99. I hesitated for a minute. Would I ever actually wear it? Would it ever pass as non-ironic? Would I find a way to not look like Blair Waldorf in the process?

The one I stumbled upon was a larger, more dramatic, heavily padded one. The more I looked at it, the more I could picture it on Sophia Loren, holding her hair back to showcase beautiful hoops and a tanned chest. A red dress made its way in, then a Tuscan backdrop, and a cool glass of Pinot Grigio. Before the Italian fantasy could fade away, I quickly added the headband to my cart and checked out. The expected delivery was 2 weeks away- plenty of time to figure out what to do with it when the time came.

Naturally, as the investigative journalist that I am, the first thing I did was Google “headbands (insert beautiful woman’s name here/ i.e. Brigitte Bardot, Ingrid Bergman, Audrey Hepburn)”. I came up with some pretty great photographs, but none were particularly helpful. It’s easy to make a headband look good when you look like that.

Next came perusing Instagram by looking to see who was tagging their headband photos with the hashtag #headband. Obviously, Carrie showed up. Tragic scene, incredible styling.

Over the next few weeks, I began to see headbands everywhere. You know when you learn a new word and suddenly start hearing it all the time? That happened with headbands. From Man Repeller to bloggers like Chiara Ferragni and Danielle Bernstein, the inspiration just kept coming.

With my research complete, and my hypothesis that I could in fact execute a few looks in a headband without looking like Blair Waldorf (save for one) prepared, I was ready. I jotted down a few ideas and waited (not so patiently) for my order to arrive. And once it did, I documented my findings in five exhibits of headband possibilities:


  1. How to wear a headband if… you’re 2018 Blair Waldorf.

I know this first header goes against the title of this piece, but I couldn’t help but wonder how Blair might translate today. The suit and Oxfords say uniform but the yellow brings it all to the 21st century. If anything is ironic here, it’s the suit, not the headband- but that’s what makes it a fun outfit- perfect for sitting on the steps of the MET, strolling around inside, or just for school.

*Suit is Zara, tee is H&M, shoes are Browns, bag is Zadig & Voltaire

2. How to wear a headband if… you still want to be ~chill~.

A bomber, ripped jeans, band tee: basically the most casual (but cool) fail-proof combination. I added patent heels to elevate the look a little, but sneakers would do just as well. I’d wear this to a concert (save for ones that might include headbanging) or to a bar with friends.

*Jacket is H&M, jeans are J. Crew, boots are Steve Madden, Grateful Dead tee

3. How to wear a headband… if you’re going out

This may not be an appropriate house party look, but I love a good blazer/jean combo to go for dinner or drinks. The sheer top dresses down both the jacket and the headband, which is more just a fun accessory to add something more trendy to an otherwise classic look. It’s one of those outfits that you’re not too sure of on paper but that ends up making you feel like a Danish fashion editor (that, on my personal scale of coolness, is the epitome of cool) once you put it on. I’ve already scheduled drinks so I can slip back into it ASAP.

*Blazer is Sandra, top is Urban Outfitters, jeans are Gap, shoes are Nasty Gal

4. How to wear a headband… if you’re lazy (or an Olsen)


The length of the blazer and the loafers really said Olsen to me, and the rest is mindless. The headband truly works here because of the simplicity- it elevates it without sticking out from an otherwise particularly plain outfit. Monochrome looks sometimes need that added accessory to spice it up- I’d love to try with a full white, pink, or mustard outfit when spring rolls around.

P.S. Closed my door to take these but my kitten, Blue, knows how sneak in. He attacked my blazer a minute later- no flowy clothes go unscathed around him.

*Jeans are J. Crew, sweater is Aritzia, blazer and shoes are Zara

5. How to wear a headband… if you just want to be fun

To stray away from the formality of a headband, I dove head in to graphics and different patterns for my last look. I wanted to be a little more extra and go full-on maximalist but this seemed more wearable. It could’ve benefitted from a red lip or bigger hoops but as is, it’s good for brunch, coffee, maybe even school once the weather warms up!

*Sweater is Maje, skirt is Sandro, booties are Sam Edelman
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