Recently in Prep Classic Category


 

Tiffany & Co. Sterling Silver Oblong Tray

Tiffany & Co. Sterling Silver Oblong Tray

Smart, sleek lines make this Tiffany Silver Oblong Tray ($425) the perfect delivery device to tote that pitcher of martinis from the kitchen to the… Read more »


Gucci Black Leather Loafers

Gucci Black Leather Loafers

UrbanPrepster does not recommend this Prep Wardrobe Essential in only one situation: The beach. In virtually every other situation, these classics are a perfect choice… 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 »


Burberry Trench Coat

Burberry Trench Coat

Another timeless classic that’s a must-have for all UrbanPrepsters. Burberry’s Trench Coat ($1695) never goes out of style. It wears just as well over a… Read more »



Alden Cordovan Tassel Loafers

Alden Cordovan Tassel Loafers

When one of UrbanPrepster’s founders was starting out on the fixed income floor of a once glorious bulge bracket investment bank, he quickly discerned that… Read more »


Nantucket Reds

Nantucket Reds

UrbanPrepster visited Murray’s Toggery Shop on Nantucket last month and picked up some new Reds. Walking around town, we were a tad jealous of the… Read more »


L.L. Bean Norwegian Sweater

L.L. Bean Norwegian Sweater

UrbanPrepster knows that this Indian Summer will be short-lived and we reluctantly admit that Autumn is upon us. With the chillier days in the Northeast… Read more »


Brooks Brothers Blue Blazer

Brooks Brothers Blue Blazer

True Prep reaffirmed that “Every single one of us - no matter the age or the gender or sexual preference - owns a blue blazer.”… Read more »


L.L. Bean Rubber Mocs

L.L. Bean Rubber Mocs

L.L. Bean started their Pillar of Preppiness with the Bean Boot (officially know as the Maine Hunting Shoe) in 1912. The low, Moc version ($64)… Read more »


Take Ivy

Take Ivy

Originally published in Japan in 1965 and just reprinted in the US for the first time this week - 45 years later! UrbanPrepster got a… Read more »


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