And though gathering style inspiration from a simple uniform may sound juvenile, you can actually make the trend your own all grown up bold shoulders, pussy bows, and tomboy influences.

If there's one thing for certain, it's that preppy fashion is always in vogue. From the crisp button-downs and bright-colored polos to tailored chinos and sweaters (casually draped over the ...

Blair, portrayed by Leighton Meester, reigned New York City as the chic preppy queen. Blair was an expert at mixing prints, made patterned tights and elaborate headbands a real-life trend, and was ...

Madelyn Cline’s ’90s-Era Headband Just in time for the anticipated season premiere of OBX on Oct. 10, Cline was a guest on The Tonight Show Starring Jimmy Fallon.

Millie Bobby Brown is channelling Blair Waldorf swapping her bob haircut for long brown extensions and a preppy headband in London.

A metallic headband with a bow fixed to the top. Both Yoonchae and Sophia wore a Versace Gianni headband, red and silver respectively.

A simple ponytail can be levelled-up with a logo hair tie. Half-up hair can be fixed into place with a bejewelled barrette, a headband can make loose hair feel extra luxe and preppy hair clips add fun ...

Sydney Sweeney attended the Miu Miu Dinner Party following the brand's PFW fashion show wearing a sparkly mini dress with a preppy collar and thick headband.

On TikTok, Gen Z’ers are swapping out shoelaces for decorative strips of all shades and taping long bows to the sides of their eyes, as if crying preppy tears.