They chest can’t get enough of this throwback swag. Flashing a little cleavage in everyday wear? As if! At least that seems to be the sentiment of the stylish tastemakers behind the “sweater vest” ...

In October 1980, Lisa Birnbach—along with Jonathan Roberts, Carol McD. Wallace, and Mason Wiley—released The Official Preppy Handbook, a satirical guide that, to this day, is considered a bible in all ...

The street style at Copenhagen Fashion Week firmly established preppy fashion as the season's standout trend, while the wide range of looks highlighted just how versatile and open to interpretation it ...

If you are looking for ways to tap into preppy styling, then you shan't look further than London. For over 40 years, London Fashion Week has been a hub for originality and rebelliousness. Adopting its ...

The intersection of hip-hop and haute couture has found its most compelling ambassador in Doechii, the rapper whose sartorial evolution reflects a broader cultural shift within the genre. Born Jaylah ...

Paige Bueckers is a one-of-a-kind superstar, and the UConn women's basketball standout brought her preppy glam look to a high-profile magazine cover. UConn women's basketball star Paige Bueckers has ...

Preppy style has been on the mood board for years at this point, but it’s starting to evolve into something new. While the look still has a bit of an academic bent, our favorite labels are moving away ...

Cameron Brink pulled up to Miami to support her Lunar Owls teammates in Unrivaled ahead of the league's playoffs in a stunning outfit for her courtside appearance. Brink was assigned to the Lunar Owls ...

“It’s not about copying a style; it’s about making it your own, interpreting it through your own sensibility,” says Octobre Éditions brand director Arthur Person, citing a Gallic passion for brighter ...

Massimo Giorgetti’s antidote to the world’s noise is focusing on clarity in design, evolving his preppy fashion with textures ...

From canonical novels to top-drawer jewelry to the roots of Ralph Lauren’s empire, test your knowledge of all things prep ...