The Unexpected Truth About Style That New York City Taught Me

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Lilly Bozzone
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Photo Credit: Belathee Photography

Photo Credit: Belathee Photography

Bowling Green . . .” I tell myself anxiously. “I take the 4 train to Bowling Green.” I check the subway map five more times to make sure I’m going in the right direction. It’s my first work commute in Manhattan. I’m pretty confident in my ability to fit in as a New Yorker . . . aside from the obvious whiplash I’m developing from checking the map after every stop.

I see my reflection in the glass of the subway doors: white oxfords, striped blue blouse, bright-red pencil skirt. “Not too shabby for the first day of work!” I nod to myself reassuringly. I put a lot of thought into this outfit. I want to look like a New Yorker, gosh darn it! Then I look over to the girl standing next to me. She’s wearing a black shift dress and black ballet flats. The girl next to her similarly wears all black. The woman beside her is also in black. That’s when I realized I was the only person on the train not wearing black.

So much for fitting in.

Where was Carrie Bradshaw in her fluffy green tutu? Or Blair Waldorf in her bright-red bow headband? Aren’t New Yorkers supposed to look like they walked off a fashion designer’s sketchpad? I thought that if I wore loud, trendy, fashion-forward items—you know, like what we see in movies or on TV—I would look like a New York woman. But it was this idea that actually drew me further away from true NYC style, not closer.

I’ve now been here for five months, and as I sit here trying to figure out an exact equation of specific items that encompass NYC style, I simply can’t. But that in itself is what makes NYC style so great; there is no exact formula. New York City is a place of unlimited fashion freedom. It is this freedom that made me, a girl from Pennsylvania (who thought she knew a thing or two about fashion), reevaluate my perception of fashion itself and the fashionable women of NYC. Here’s what I’ve observed.

01. Black on Black

Did I mention that New Yorkers wear a lot of black? Pretty dreary and boring, right? Wrong.

The New York City woman has a talent for styling her black pieces into sharp, intelligent, and unique outfits. Sleek tailored pants, quality leather jackets, ankle booties with gold buckles, structured asymmetrical wrap skirts, purses and bags—against the backdrop of a crazy city, it’s pretty hard to deny that all things black are sleek.

When I can’t afford the high-quality designer stuff (which is all the time), I remember that the real key to wearing black on black is choosing pieces that truly flatter you. Black is basic, yes. But it’s also a limitless canvas. Different styles, silhouettes, and details can turn a black outfit into something really unique.

02. Elements of Color and Embellishment

I have an Asos shopping cart full of accessories that will forever live in online shopping limbo—that is, until I win the New York lotto. Why? Because living in NYC has opened my eyes to the power of accessories.

Remember what I said about black being a canvas? A black-on-black wardrobe doesn’t mean that the New York City woman is afraid of taking fashion risks. On the contrary, she uses black as a way to make her accessories stand out. Often, it is the accessories that make an outfit iconic. Tartan-print handbags, leopard-print pointy flats, giant cat-eye sunglasses, bright-red bucket bags, glimmering oversize gold watches, buckles, studs, and zippers . . . the New York City woman knows that the devil is in the details.

03. A Touch of Messy

After a few days of riding the subway system, I learned that New Yorkers are the busiest people on the planet. Time is a commodity, and efficiency is king. Getting ready in the morning is a scant period of time for just about any woman. For a New Yorker, this time is even more truncated by commuting. When unexpected train delays occur at any given time (especially when you’re already late), the best approach is to leave one hour early no matter what. That means less time for prework primping.

New York City women have mastered the art of messy. But what does “messy” mean? It doesn’t mean sloppy or disheveled. “Manhattan messy” means undone hair, unstyled and loosely lying where it pleases. It means structured blazers with pushed-up sleeves, white button-ups half tucked in, simple makeup, and oversize bags concealing commuter sneakers and holding everything the NYC woman might need to take on the city.

04. Stylish Utility

The New York City woman does not mess around when it comes to form and function. She is on the go from 7 a.m. until at least 6 p.m. but often later. As she’s schlepping down avenues, climbing up subway stairs, waiting for her Uber, pushing past tourists, or keeping steady on a bumpy 4 train, the NYC woman knows how to be both stylish and comfortable. I mean, she’s got stuff to do! She can’t be worrying about how her clothes look when she’s taking life by the horns.

This means breathable cotton fabrics and flowing tops that are both comfortable and dressy and look great tucked in or pulled out. She knows how to style sleek joggers into a professional outfit, and she has an eye for longer skirts that don’t ride up as she power walks her way to work. The high heels of Sex and the City and Gossip Girl make for lofty ideals, but in the end, every smart New Yorker chooses comfort over pain. But it’s not at the expense of style. It seems like every New York City woman has a pair of stylish flats, be they sneakers, ballet flats, or booties. Massive purses in quality leather abound. In NYC, you will see it, and it will look good.

05. Never Overthinking

Before I moved to New York, I used to stand in the mirror and ask myself, “Is this a little . . . too crazy? Will people look at me like Im weird?” Often, I’d take off that outfit and wear a toned-down version instead. Now, I put on exactly what I want and march out the door without even thinking. I learned that the New York City woman dresses with purpose but doesn’t think too long about it; she acts on instinct and trusts her fashion choices. There is something so healthy about not fussing over your reflection in the morning and wondering how people are going to look at you. The focus when getting ready every day is not on the clothes themselves but on the woman wearing them.

The reason why I can’t boil NYC style down to an exact formula is because I can’t see past the woman to the clothes. The style of the New York City woman calls you to refocus on who she is (or who you are) rather than on trends. My perception of fashion in relation to the women changed when I realized this: We aren’t just feet wearing Louboutin heels or arms wearing leather jackets or necks wearing statement necklaces. We aren’t just parts. NYC style taught me that each woman is a unique whole person, body and soul. The fashion in this wonderfully chaotic city celebrates a woman, not what she is wearing.

When I first moved to NYC, all I wanted was to fit in. Little did I know that the key to fitting in was actually not fitting in. Now when I get ready every day and look at my clothes, I think, “How can I be myself . . . more?”