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. 

Retro hair accessories have been making quite the comeback, and bows are one of the simplest ways to play with the trend. Add a headband with a big, patterned bow over the side to give your hair sophisticated and feminine look. The side placement will keep the look from appearing too juvenile. Keep your hair down for a softer, more classic preppy ensemble, or put your locks up to let the bow do all the talking.

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.

A headband can be a great way to style natural curls and nail prep style without a ton of extra effort. Place a colorful headband on top of your hair and push the front part of your locks back, letting your natural texture show from the back. Choosing a glitzy headband with a bunch of gems can be an easy way to jazz up the look at make it look extra fancy, which is great for if you're going for a slightly more glam pretty style.

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.

Curtain bangs are a great hairstyle to rock because they give you the option of pulling a bit of hair from your headband to frame your face. They are also oh so classically "Gossip Girl," with their wispy sides perfectly swooshing out at the cheekbone. Wear yours with a simple cloth headband to let the face-framing layers do their thing, while channeling the ultimate prep girl look.

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.

Just because you're using the headband to create a style, it doesn't mean you have to just leave your hair as is. An easy braid along one side of the head is a great way to vary up a preppy look without trying super hard. Tuck yours behind the ear so that you can show off some hoops or a perfectly curated ear-stack.

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.

Not all headbands have to be super structured to complete your preppy look. Combine preppy and sporty by using an elastic hairband to not only keep your hair out of your face, but give a traditionally feminine aesthetic some active energy. Place it toward the top of your forehead and let your hair fall down the sides for the ultimate cool-girl look. Match the headband with your outfit for a monochrome look like this is totally chic.

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.

Silk is perfect for a preppy vibe as it has that air of elegance and money — but it's also practical as it will help you take care of your hair at the same time. That's because silk can prevent things like hair snagging that plastic headbands can't. Best of all, it looks great with any style — be it longer, curled hair, or pulled up into a ponytail.

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.

Though it's been popular for a while now to curl the hair away from the face, for an extra preppy look, curling the ends of your locks inwards is so in. The look works best with hair that's around check length, but anyone with tresses long enough to curl under can recreate this style at home. Use a plush headband to keep every layer falling in the right places, with the front pieces tucked behind for a simple vibe that screams "Gilmore Girls."

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.

There are loads of ways to do a low pony, but this one in particular is great for those looking to get preppy. We love this twist on what could be a pretty simple hairstyle, as well as the way the headband has literally been incorporated into the hair twists to really make the band part of the 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.

The preppy style is all about that mix of sophistication and youthfulness, and pigtail braids are a great mix of the two. This style could be finished with a soft, cloth headband, or chunky material headpiece to draw the eyes upward. Equally, curling the ends of your locks will add yet another unique twist.

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.

If you'd rather not your hair detract from your sophisticated and chic outfit, sporting the '90s cloth headband trend is the way to go. If your hair is naturally dark, choosing a headband in black or dark brown will grant you all the style benefits of a headband — such as taming flyaways — while letting your hair appear relatively effortless. This look can also be great if you want something a bit more sporty. 

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. 

Most people likely think of buns as a staple style of balletcore, but if you want to give yours a preppy flourish, then a headband is just right. A colorful headband in a blue shade can also be a great way to give a slicked back look some playfulness — perfect for those who maybe aren't a fan of styles that appear too scraped back without much texture.

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.

You don't have to have all of your hair either in front of or behind your headband. If you like the idea of your hair framing your face, pull a few strands down through the headband so it falls closer to your face. A stretchy pink gingham headband with a knot in the center is perfect for nailing a traditionally feminine, preppy aesthetic.

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. 

Why not step out the box and place two headbands on your head? If you've got a pixie cut, double bands in contrasting colors can be a great way to draw attention upward toward your beautiful, edgy hair.  No matter the color, keep your headbands on the thinner side if you're trying this idea, as two may be a little overwhelming (and difficult to wear!)