Recently in Prep Classic Category

L.L.Bean Black Bean Boot

Now this is so UP. Just when we thought the Bean Boot couldn’t get any better, our friends in Freeport have given us urban dwellers… Read more »

L.L. Bean Blucher Mocs

Depending on how old you are, you either recall a time when you had to sport a beat-up pair of these with your ill-fitting blue… Read more »

Polo Ralph Lauren White Oxford Shirt

From the Prep staples collection. What ever happened to the classic oxford cloth shirt? Ralph still has them. While we have tried to keep up… Read more »

Johnston & Murphy White Bucks

One of our founders has a rule that he knows is ridiculous, yet he still can’t allow himself to break it: Gin & Tonics and… Read more »

Charles Tyrwhitt Women’s White Non-Iron Classic Shirt

Our lifelong quest for the perfect ladies’ white shirt is finally over. Charles Tyrwhitt’s Classic Shirt ($160) requires no ironing and always looks crisp -… Read more »

Jack Purcell Garment Dyed Oxfords

The Preppy Set’s answer to the ubiquitous Chuck Taylor, Jack Purcell Oxfords ($50) may be the perfect sneaker. With Converse’s Garment Dyed line of Purcells… Read more »

L.L. Bean Goose Down Vest

Snow, sleet and freezing rain call for serious outerwear. But UrbanPrepsters donning vests is a surer sign of early spring than cherry blossom buds in… Read more »

J. Press Grey Plain Front Merino Wool Trousers

From the wardrobe building blocks collection. Any Preppy man who doesn’t own a pair of these J.Press Grey Merino Wool Trousers ($175) is, well…not a… Read more »

Burberry Big Check Cashmere Scarf

UrbanPrepster can’t believe November has arrived, and while we will miss our seersucker and polo shirts, we are pleased that the temperature has dipped low… Read more »

Cartier Tank Watch

We bet you’ll wear this ladies’ Cartier Tank Watch ($3,095) more often than your pearls. It’s beautifully sophisticated, yet fabricated from stainless steel and built… Read more »