Rihanna is one A-lister who knows how to marry posh and sporty pieces together. This fall, one of her most casual cool-girl looks is trending, and we can’t stop swooning over it. Enter: rugby shirts.

Preppy style may not have ever fully left—we’d argue it’s one of the few truly evergreen menswear aesthetics, and one that almost every guy has dipped a (loafer-clad) toe into at some point—but it’s ...

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 ...

Gen Alpha may throw 'preppy' around as an insult, but little do they know, it's making a major comeback as a stylish fashion trend this fall. These Mary Jane flats are the ultimate preppy chic fall. I ...

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 ...

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 ...

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 ...

When you purchase through links on our site, we may earn commission. Read our full commerce guidelines here. For many of us, polo shirts conjure up images of golf Dads, posh trust-fund heirs, or ...

When Meghann Fahy’s Devon arrives on the fictional island of Port Haven in the new Netflix series Sirens, she takes one look at the crowd and offers the following commentary: “What is this place, and ...

PureWow editors select every item that appears on this page, and some items may be gifted to us. Additionally, PureWow may earn compensation through affiliate links within the story. All prices are ...

The preppy Princeton murder suspect accused of ripping out his little brother’s eyeball after beating and slashing him to death tried to kill himself inside his jail cell Thursday night, a law ...