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

Preppy chic is back – and it’s surprisingly affordable ...

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

India, Jan. 13 -- After the performative man was exposed on Instagram, he knew his days of tote bags, baggy jeans, and matcha ...

From tweed jackets to prairie dresses, Tuckernuck’s preppy, classic style has quietly become a favorite among conservative ...

Braving the cold never looked so good ...

This shoe was made for walking, but it's got plenty of styling potential too ...

Throughout his career, the late Grateful Dead guitarist wore polo shirts, bolo ties, and thigh-bearing shorts with an ...

They're giving rich.

I’m not exactly sure why I put off mastering how to style corduroy pants for so long. It’s not that I don’t like the look—I just never thought the soft, textured bottoms were my sartorial vibe, per se ...

Sure, we all know how to style socks; most of us do it every day. But often, the result is, well, sauceless. When you’re in ...