25 Headband Hairstyle Ideas For The Perfect Preppy Look

If you ever saw the original "Gossip Girl" on The CW, you know exactly what we mean when we say a preppy headband look. Leighton Meester's "Blair Waldorf" was pretty much the queen of this style, featuring a polished, yet attention grabbing headband with a fashion-forward wardrobe. For those unfamiliar with the Upper East Siders of yesteryear,  allow us to explain what preppy fashion really is: The term actually originated as a way to describe the style of prep school students on the East Coast. So, think pieces like blazers, sweaters, button downs, and pleated skirts. The term preppy can also incorporate certain patterns too, such as polka dots, argyle, or plaid.

Since so much of the prep look is about uniformity, one place where people have long showcased their individuality is with accessories. And the ultimate staple piece for creating that preppy look will forever be the headband. Now, with hair accessories becoming  From bold, plush bands, to embellished thin styles, any version of the hairpiece goes when it comes to creating your preppy style. As long as you style it the right way, of course. 

For a cute twist on the classic preppy headband look that works beautifully with short hair, try playing with braids. A half braided crown style will automatically create more intrigue than simply sticking a headband on your hair when it's down because it creates shape and volume. To try it yourself, form a small French braid at the front of your hair and tuck its tail end above your ear under a thick, lacy headband. Let the rest of your hair fall down naturally for a classic, polished style that looks practically debutante-ball ready without a ton of effort.

Pearls are a timeless accessory, and wearing them on a headband is a great way to add a touch of playfulness to an otherwise vintage style. Take a delicate, thin headband adorned with pearls and wear it with a structured, middle part. 

Keeping your hair down in soft waves under the headband will only add to that clean elegance.

Another way to get chic with your preppy hairband is to push the front part of your hair back with it to really make a statement. A black and white polka-dot headband paired look over poker straight, combed hair is a great way to pay homage to classic prep style of the 1960s. The mix of the playful pattern with simple, understated colors gives the style a modern and sleek edge.

You don't have to wear all of your hair down for a chic headband look, though. And this look proves that. Give your preppy hair an edgy and modern twist by adding lines of braids at the crown where your normally slicked back part would be. Let the rest of your hair fall naturally, or blow it out for a wavy look that's as good with a plain tee shirt as it is with a blazer and blouse.

No one's saying you need to go small when it comes to headbands. An oversized version of the accessory can really bring your outfit together, and it looks amazing with a sleek bob hairstyle. Especially when positioned to let just a little hair fall beside the face for a more natural effect.

An  embellished headband can be particularly stunning when paired with natural curls. On top a head of spirals, the super sparkly accessory almost looks like a crown or tiara, allowing each curl to stick out without appearing too frizzy. This look could easily be paired with a super preppy beige sweater and neutral flannel skirt for total "Gossip Girl" vibes.

A bold headband deserves its own moment sometimes. So if you're ready to put the hair accessory firmly in the spotlight, then the best way to do that may be to slick your hair back so your headband becomes the focal point. A pearl adorned headband that's almost hat-like is a great way to serve elegant, vintage vibes will staying true to prep style. Pair with a super-slicked back bun to not overwhelm the top half of your look.

Although headbands have long been known for how they help long-haired folks keep their strands out of their face, they can look amazing on short hair, too. A thicker headband on a pixie can add texture and dimension, especially if you have microbangs.

Preppy hair is usually a little more undone and understated, so letting your locks fall over your shoulder in a low pony with a headband pushing it away from the face is a great way to channel the aesthetic. It's a look that's casual enough to wear to the tennis club or drinks with friends, while still looking more put-together than a basic ponytail.

As headbands can be so critical to the preppy look, there's nothing wrong with using it to make a serious statement. A thicker black headband adorned with accessories, such as pearls or spikes, can really work with a preppy outfit. Keeping your hair softer and with loose waves will keep things on the casual side. 

To really put a twist on the classic preppy headband, play around with working the accessory into your hair — literally. Using a headband with extra ribbon, weave braided strands of hair with the accessory. Stick with a print like blue polka dots for a pop of color and excitement.

Another unique look ditching the plastic headband involves adding a topknot to the back of your head only, with the headband placed further forward on the head. it still keeps everything together, while allowing the rest of the hair to fall naturally. Go for gingham or tartan to stick with classic prep, or modernize it with leopard or paisley.