Recently in Offspring Category

Vineyard Vines Crazy Bands

Your offspring will always find ways to express themselves through the latest fads, despite your efforts to indoctrinate them into the timeless Preppy aesthetic. Enter… Read more »

Chesapeake Ribbons Owl Belt

Ribbon belts are an instantly recognizable sign that you’re a true Prep. But unlike staples such as the blue blazer, they allow one to cheerfully… Read more »

Patagonia Baby Synch Booties

It’s important to familiarize your offspring with fleece at a very young age, lest you risk them not taking to it when they grow older.… Read more »

Brooks Brothers iCatalog App for iPad

How does a company that has been outfitting the conservative Prep for the last 193 years stay relevant? By presenting their classics and newest lines… Read more »

Create-Your-Own Boy Long-Sleeved Polo

It’s never too early to get little Skip familiar with the collared and monogrammed look that he’ll feel naked without later in life. This charming… Read more »

Petit Tresor Pedal-Car Racer

It is never too early to teach UrbanPrepsters-in-training that getting there and showing you have arrived are two different concepts. The Petit Tresor Pedal-Car Racer… Read more »

Little Miss Stripes Binker Pacifier Clip

UrbanPrepster is open to tolerating “binkies” provided they feature elements of Prep style. This grosgrain ribbon inspired pacifier clip ($8) is sure to position your… 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 »

Ralph Lauren Girls’ Black Velvet Dress

Men and boys have their Brooks Brothers Blue Blazer. For Miss UrbanPrepster, Ralph Lauren offers the adorable Tillie Velvet Dress ($150). What better time than… Read more »

Personalized Embroidered Diaper Cover

At one end of the spectrum is the baby with the disposable diaper on and little else. At our end is the precious offspring appropriately… Read more »