Preppy in New York City

Union Square and 17th Street, New York, NY — Union Square and 17th Street in New York City (1998)

My wife took this photo of me looking at books among the vendors at Union Square near 17th Street in New York City. As best I can recall, this was taken around December of 1997. We had been in the city nearly a year, having moved up from South Carolina, and I was working for MoMA.

Union Square was a seven minute subway ride on the L Train from the Bedford Avenue stop in our neighborhood: Williamsburg, Brooklyn. The World Trade Towers are visible to the right, just beyond the pedestrians. Washington Square Park was a short walk south down University Place in the direction of the towers.

My sartorial style was largely out of synch with the burgeoning hipster population of Williamsburg, but drew respect from our old school Italian neighbors. In this photo, I was wearing charcoal gray wool flannel pants, a button down shirt, a wool argyle sweater (non-thrifted Christmas gift) from Brooks Brothers, a wool herringbone pattern topcoat and a pair of black Bass Weejuns. The glasses were tortoise rim.

I’m not sure whether to love or hate the fact that hipsters have appropriated (maybe hijacked is a better word) the preppy look in the last few years. They are certainly dressing better. I suppose that is a good thing. So I won’t complain too much about their “preppy with a twist” aesthetic. How ironic! When walking down Bedford Avenue once in the late 90s in khakis, a ribbon belt and a pink button down, I felt as though I was doing a perp walk based on the scornful looks I received. That preppy has been embraced by the same kind of people proves good taste never really goes out of style, even if for them it is a fad. You can read more about hipsters on Free Williamsburg. (Note: after I made this post, I found this related article published in The New York Times: “How I Became a Hipster.”

On the same day as the Union Square photo, my wife and I went uptown to see a Broadway show at the Neil Simon Theatre. I can’t remember which show it was. Maybe I can track that down by going through some old playbills. A Christmas tree is visible on the balcony above the Russian Samovar restaurant next door to the theatre.