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 ...

We may earn commission from links on this page, but we only recommend products we love. Promise. Scroll on to see a list of 25 preppy clothing brands that deserve a spot in your closet. Whatever ...

On a recent Tuesday afternoon, a student of mine wore an attention-grabbing baseball cap to class. The brim was frayed and worn, and the word COCKS was stitched in block letters across the front. I ...

Welcome to Town & Country’s first-ever Preppy Awards, a celebration of heritage brands and classic pieces that have achieved icon status in the world of prep.

If you buy something through my links, I may earn a commission. Ever wondered how to pull off that iconic preppy golf style while watching a Masters tournament and cheering your favorite player? My ...

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 ...