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Omega Seamaster Planet Ocean Chrono

Omega Seamaster Planet Ocean Chrono

An expensive sailor’s chronograph watch is a great choice when building your collection of hand-me-downs for Kip and Biff to fight over. UrbanPrepster won’t judge… Read more »


Personal Polo Horse

Personal Polo Horse

Eat your heart out Ralph Lauren. Take the Polo pony lifestyle to the extreme, as well as shock all the gents at the Club, when… Read more »



Deerfield Academy

Deerfield Academy

Considered one of the Preppiest boarding schools in the country alongside Exeter, Choate and Andover. Established in 1797, Deerfield Academy ($43,800/year) sends the majority of… Read more »


La Cornue Grand Palais 180

La Cornue Grand Palais 180

Customization is right up there with monogramming in the world of Prep, and this La Cornue Grand Palais 180 from Joanne Hudson Basics ($46,000), which… Read more »



BMW M6 Convertible

BMW M6 Convertible

The BMW M6 ($119,000) 5.0-liter, V-10 engine allows the UrbanPrepster to combine all of his finest attributes with one push of its keyless ignition: elegance,… Read more »


Rock Meadow Estate

Rock Meadow Estate

This lush Prepster crib may be a teeny bit out of reach for most Thomas Pink or Brooks Brothers-clad arms, but one can dream, right?… Read more »


Mikimoto Cultured Pearl Necklace

Mikimoto Cultured Pearl Necklace

An 18” single strand of real pearls is a must-have in every Preppy girl’s jewelry collection. Mikimoto’s White Cultured Pearls ($2,300) are the perfect luxurious… Read more »


Your Own Private Island

Your Own Private Island

Owned by Virgin founder Sir Richard Branson, Necker Island operates as a resort and is part of the Virgin Limited Edition portfolio of luxury properties.… Read more »


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