Springtime in New York

Where shopping is concerned, New Yorkers aren’t just on another continent, they are on another planet. For the purposes of anthropological study, I’m going to narrow down that sweeping statement and concentrate on one area of Manhattan in particular, which is where, in my opinion, the purest and most extreme form of mad Manhattan dressing and purchasing takes place—the Upper East Side (or UES, as it shall now be known). The neighborhood, which stretches roughly from 59th Street up to 96th Street, is where the majority of Manhattan’s elite private schools are housed. It has some of the most expensive real estate (the closer to Fifth Avenue, the more expensive); the chicest shopping areas (Madison Avenue, from 59th to 88th Street); the highest percentage of nannies, yummy mummies, soccer moms and dog walkers; the greatest number of doctors and plastic surgeons; endless traffic jams of chauffeur-driven, black Chevy Suburbans; and two of the world’s most preposterously Eurotrash cafés—Sant Ambroeus, known as St. A, and Via Quadronno, or Via Q.

Gossip Girl Fashion

If you need further explanation, let’s just say that Madonna has ended up on the UES; Jackie Kennedy Onassis used to walk the Central Park Reservoir daily from her home on Fifth Avenue; Tory Burch, the designer who borrowed the style of the Upper East Sider, repackaged it and sold it back to them, resides in a favorite UES watering holes, the clubby, grand Pierre Hotel; and Mickey Drexler, chairman and CEO of J. Crew, the brand of all wannabe prepsters, lives in the area, too.

Before we get to the shopping itself, let’s discuss what Upper East Siders wear to shop in. It’s a given that all New Yorkers are immune to fashion trends, having, as they do, specific uniforms for particular climates and seasons, regardless of what comes down the runway. Nowhere is this more apparent than on the UES, where even the teenagers from private schools like Nightingale, Spence and Chapin (girls), and Buckley and St. Bernards (boys) have their own particular “thing” going on, as “Gossip Girl” captures so well. For the girls, it’s short school skirts, bare legs (regardless of the weather), lots of blown-out hair and baggy Westwood boots; for the boys, it’s a kind of baggy, subversive prep—Ralph Lauren meets P. Diddy, complete with acid-colored Ralph Lauren polo shirts, baggy khakis and Moncler puffer jackets.