For anyone who grew up in the late ’90s/early 2000s, being called “preppy” definitely drummed up a lot of specific images: crisp, pastel polos and pleated skirts, cable-knit sweaters around the ...

We all know what "preppy" means — don't we? If you're older than those in Generation Alpha (anyone born after 2012) you might think of a wealthy person with a particular fashion sense (collared shirts ...

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." On the hunt for your new favorite athleisure shoe? Reformation and Hoka's debut sneaker collaboration may ...

Seiko is back with a trio of preppy-coded King Seiko time-tellers, each boasting a distinct color dial: “Preppy Blue,” “Preppy Green” and “Preppy Burgundy.” The choice of colorways is inspired by the ...

With the release of Challengers a day away, Zendaya has been squeezing as many tennis-inspired looks into the press tour as she can. On Wednesday alone, she was photographed in three different outfits ...

We all know what "preppy" means — don't we? If you're older than those in Generation Alpha (anyone born after 2012) you might think of a wealthy person with a particular fashion sense (collared shirts ...

Every item on this page was chosen by a Town & Country editor. We may earn commission on some of the items you choose to buy. On the hunt for your new favorite athleisure shoe? Reformation and Hoka's ...