If you ever saw the original "Gossip Girl" on The CW, you know exactly what we mean when we say a preppy headband look.

The 27-year-old, who has yet to post the fit on her main grid, shared a sneak peek to her Instagram stories, and honestly, we ...

Then, on Wednesday (November 13), the model went out with her new hair on display. She wore a preppy look for fall, pairing a ...

Camila Cabello paired a Blair Waldorf-coded prep school skirt with a sheer top and visible bra in a schoolcore outfit shared ...

It was only fitting for Lisa’s first outfit to come from a master of twisted preppy style: Thom Browne. The singer slipped into a graphic cardigan and matching t-shirt, both printed with a navy ...

Selena Gomez loves a shimmery red-carpet moment just as much as she loves a preppy schoolgirl street style look. And with her ...

At least that seems to be the sentiment of the stylish tastemakers behind the “sweater vest” trend — a revival of the 1990s preppy top arising ... reawakened yuppie look isn’t just ...

In the clip, a girl was filmed walking into the store ... A significant amount of content about the new preppy style is also by people baffled by it, saying the "preppy" they remember was vastly ...

Selena Gomez loves a shimmery red-carpet moment just as much as she loves a preppy schoolgirl street style look. And with her latest ensemble, she proved she can have them both. The actor was a ...

Thanks to the kids, preppy style is having a major moment. Miu Miu kicked it off last spring on the catwalk. Now, Polo by Ralph Lauren is huge among 15-year-olds. Pleated skirts are everywhere ...

Anytime you want to radiate a classic, youthful energy, the preppy style has got your back. The style’s roots can be traced back to the old-school Ivy League and other classic collegiate looks.