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The Guide to Being a 1920s Hipster

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A journey into Gatsby-era New York, as inspired by the NYT's brave anthropological study of Brooklyn Hipsterdom

You know you’re in 1920’s New York when someone in a pinstripe suit and a bowler hat tells you that his line of work is “night-running bathtub gin.” 

I’m locked in a conversation with a stoic sort of alcohol salesman who spends his nights shuttling illegal grain alcohol from port to port, and his day drinking said alcohol. He smells perpetually of musky, hand-distilled liquor. He is the essence of DIY.

“Is it locally produced?” I ask, in an ill-concealed attempt to blend in. His only answer is a wry smile.

O, Bohemia! I’m confused, and fairly frightened by it, like a newly born duckling struggling with its first brave steps. I want to become a flapper, become a part of this community I've heard and read so much about. After giving the matter the calculated consideration of a father naming his first-born son, I’ve decided that the only way to fully understand their culture is to immerse myself in all its unwashed beauty.

In all of its smoky saloons, and long stemmed cigarettes, and women with men’s haircuts—a thing I do not pretend to understand. 

And so this 42-year-old avowed Victorian woman (born 1880) pledged to spend two uncomfortable nights exploring this commodified urban landscape of youth in New York City. It’s strange, having been born on the cusp of this, shall we say, cultural shift—I am at once acutely attuned to and removed from it. I am not a flapper, but if not for my advanced age and dislike of feathers, I could have been one. 

The first night I checked into the Plaza Hotel, awash in warm light and plush carpeting—a mixture of old world elegance and decidedly new world ideals. The tea garden out back was littered with provocative urban transplants younger and more wild than myself, unaware of, or perhaps unconcerned with, the volume of their speech.

I left the hotel and began to walk along Fifth Avenue, a veritable ocean of waxed mustaches. Though appealing, I felt it wasn't a shave that my feminine facade needed, but rather an instrument of disguise. I stopped by DeLacy’s hat shop on Park Avenue to begin my transformation. I was taken aback by the owner’s almost immediate input regarding my appearance. “You look like quite a high hat doll,” she yelped, which I was later told meant I looked like a snob. I reminded myself not to take her judgment seriously. This is the way of the flappers, I thought, and how can I turn their lives into an anthropological study if I don’t keep an open mind? I told her: “I’m going for a Zelda Fitzgerald look. I want to look like a flailing ballerina with the potential to be ruined by mental instability.” 

She fashioned me with a deep chocolate mink hat, but I felt like the fur made my nose tingle. After many false starts, we settled on a forest green cloche hat, which I bought for $27. Gaining confidence in my flapper assimilation, I again asked, “Was this made locally?”

Next I stopped to get a sugary midday pick-me-up at the local chocolate shop, Schrafft’s. I felt uneasy surrounded by the pretentious display of cocoa in all its possible incarnations: bars, and balls, and bigger bars. But I reminded myself to act natural, cool, like a flapper would. “I’ll bet all of your clothes smell like chocolate,” I whisper to the freckled young woman behind the counter. “They do,” she offered. 

That night,  I visited a jazz club called Leon & Eddie’s on 52nd St. I’m told 52nd street is the epicenter of jazz culture, and Leon & Eddie’s is the bee's sneeze, or something like that. I was hoping to catch a glimpse of Josephine Baker, who I was told is a frequent visitor of the club, but the rooms were so clouded with smoke I probably wouldn’t have seen her even if she had been standing next to me. The patrons of the club were unlike anyone I had ever met before, openly mouth-kissing and frequently flirting, touching each other with the playful air of hormonal peacocks attempting to attract a mate. Sitting alone, I wondered aloud if the ivory in the musician’s piano keys was locally sourced. A man in the neighboring booth was talking to a woman I’m certain was his mistress. I say this because she called him “Daddy,” but not in a way you would talk to a man you shared blood with. There was a tone. 

Pulling my new hat closer to my scalp, I felt I had truly integrated into the flapper culture. Like a lioness, against all odds, blending into a herd of mustachioed zebras. I danced with several young men, each with his hat slightly askew, and sporting suit jackets much shorter than the ones I was used to men wearing. One of these renegades tried to take me outside to do what he called “necking,” though really my neck was only the half of it. 

I pulled away and said with practiced ease, “Sorry if I'm giving you the icy mitt,” which is apparently something the kids say. 

Correction: An earlier version of this article referred incorrectly to the shapes of chocolates available at Schrafft's. They are not offered in the likeness of future U.S. President Harry Truman.