Recently in Leisure Category

The Catcher in the Rye

UrbanPrepsters were forced to read many works of literature in the seemingly endless years of matriculating through the most expensive schools in the nation. None… Read more »

Smathers and Branson Clover Needlepoint Flask

For the uninitiated, St. Patrick’s Day consists of dressing all in green, adorning outlandish headgear, and stumbling around the nearest parade-hosting town with a can… Read more »

Morgan 3 Wheeler

If a set of spinning chrome rims and neon running lights does not fit your idea of a custom vehicle, we have a suggestion: the… Read more »

Contra by Vampire Weekend

Let’s be honest. Indie rock bands are not typically the realm into which UrbanPrepsters delve. But when a band releases a song called Cape Cod… Read more »

Rushmore - Criterion Collection

The academic aspiration of a true UrbanPrepster is not just to “prep,” but to get kicked out in style. In Rushmore ($38), our hero Max… Read more »

Grand Wagoneer Woodie Restorations

UrbanPrepsters of a certain age will fondly recall piling in to Mummy and Father’s Jeep Grand Wagoneer for long drives to the beach or the… Read more »

Trading Places (Special Collector’s Edition)

“Looking good Louis.” “Feeling good Billy Ray.” Dan Akroyd was thoroughly underrated as Louis Winthorpe III beside Eddie Murphy at the height of his stardom.… Read more »

L.L.Bean Classic Toboggan

We all know that cheap plastic saucers are for church fundraisers. When you bundle up the offspring and head out to that slope by the… Read more »

The Nantucket Holiday Table

Despite what the discount retailers having been marketing to us, we at UP firmly believe that the Christmas Season doesn’t officially begin until the last… Read more »

Lilly Pulitzer Secret Garden Nook Cover

UrbanPrepster knows how vital it is to judge a book by its cover. And when someone, or something, is draped in Lilly, immediate acceptance is… Read more »