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 ...

Trust TikTok to coin a new hair trend. Heading into autumn, the #preppyaesthetic is trending with crisp-collared button-downs, blazers, and loafers. And preppy-girl hair is the perfect companion.

NEW YORK - NOVEMBER 27: Leighton Meester, Chace Crawford and Blake Lively on location for "Gossip Girl" November 27, 2007 in New York City. (Photo by James Devaney/WireImage) Of course, certain styles ...

CLEVELAND, Ohio – According to tweens, preppy has a new meaning. Preppy no longer refers to the G.H. Bass Bucks, penny loafers or V-neck tennis sweaters I wore with matching turtlenecks in middle ...

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. No outfit is complete without the perfect pair of shoes. From embroidered ...

CHLOE LEE never thought she’d be grateful for her school uniform. For nearly a decade, Ms. Lee, who is now 24 and founded the fashion-resale app Selleb, wore “the same blue blazer, pleated skirt, ...

All the Latest Game Footage and Images from Custom Order Maid 3D2: Overbearing and Preppy Girl Maid GP-01 "Preppy Girl Maid" is now compatible with the following content added in "Custom Order Maid ...

This is an archived article and the information in the article may be outdated. Please look at the time stamp on the story to see when it was last updated. Authorities are searching for a man dressed ...

All the Latest Game Footage and Images from Custom Order Maid 3D2: Overbearing and Preppy Girl Maid GP-02 "Preppy Girl Maid" is now compatible with the following content added in "Custom Order Maid ...