If there were a Hall of Fame for classic preppy essentials, the J.Press Shaggy Dog would undoubtedly be the first inductee. The brand recently teamed up with Alex Mill for a collaboration that ...

Every so often, a fashion show triggers a zeitgeist shift. More than any breathless praise or armchair analysis, it is a gut feeling that these clothes are going to change the way we dress. While ...

Today’s collection was a natural continuation of the July runway show, as if the previous event was a chapter that had no concrete end, but rather a slow summer interlude—something that the designer ...

In the winter of 2020, my neighbor in Sing Sing told me that there was a true crime documentary on TV about Robert Chambers. The Preppy Murder: Death in Central Park was an AMC limited docuseries that ...

Oxford shirts, penny loafers and crisp chinos are just some of the staples that make up preppy style, an esthetic originally associated with prep schoolers and the Ivy League and closely tied to ...

With summer coming to an end and the kids heading back-to-school, celebrity stylist Tiffany Reid joins TODAY to share trending looks for kids this fall including a twist on the preppy style, denim on ...

You'll want to study up on these looks. Sometimes getting dressed up in the summer can be such a hassle. Thankfully, a shirtdress is a one-and-done style that eliminates the guesswork from your ...

A wealthy Connecticut suburb has been rocked by the killing of a private school lacrosse star stabbed to death at a house party. Raul Elias Valle, now 20, is accused of killing 17-year-old James ...

Preppies have bestridden the earth with their very own specific swagger, even sprezzatura, doubtless in variants of the Sperry Top-Sider deck shoe, for many decades and probably centuries. The ...

The quirky Los Angeles-based hotel chain took an old roadside motel off the Coast Highway and turned it into its latest preppy-meets-Parisian bed-and-breakfast-style boutique By Benjamin Svetkey ...