How to Dress Like a New Yorker on Your Next Trip to The Big Apple

How to Dress Like a New Yorker on Your Next Trip to The Big Apple

A few weekends ago I had the wonderful experience of spending a fall weekend in New York. As I wandered through the Met, moseyed through Central Park and got delightfully lost in the West Village, the thought that tickled me most is that these were the same streets that featured so many beloved films and TV. All of my Meg Ryan favorites, including When Harry Met Sally, You Got Mail, but also modern favorites like Set it Up and Sleeping with Other People. They are currently filming the Sex and the City Reboot, and given I binged watched the series again this Spring I kept hoping to spot Sarah Jessica Parker every time I turned the corner. Side note, if you are also excited about And Just Like That, I highly recommend listening to Sentimental Garbage podcast in which novelists Dolly Alderton and Caroline O’Donoghue review each SATC season for the great American novel that they are. There’s something about New York that lends itself to film don’t you think? And while I’m betraying myself as a decidedly un-jaded and dreamer of a human, you can feel that energy, that magic even if you’re only there for 48 hours.

Despite my starry eyes for the city’s skyline, I managed to get asked for directions not once but twice while there. Whenever I travel I count it as a personal victory if I can manage to pass as a local. This trip, it helped that my outfits were straight out of New Yorker in Autumn lookbook. Not only is it fun to dress like the locals when visiting another city or country, I’ve also found it makes the experience of traveling as woman, especially solo, a lot easier when you blend in and look like you belong. Obviously, this isn’t completely possible depending on where you are in the world (especially for BIPOC women), but making that effort does go a long way. So without further ado, here were my outfits in NYC, where I wore them and why they were quintessentially “New York”.

I’m the type who likes her travel outfits to be comfy but also look polished. My favorite pair of mom jeans, a black tank top, a tweed blazer and boots was Outfit 1. I had a little carry on and my Stories Studio tote, and this Phillip Lim chocolate croco crossbody bag.

Once I had arrived in NYC, and gotten settled in at my hotel The Evelyn NYC which is located right above the Flatiron and Madison Square Park, I changed and headed to lunch. Outfit 2 for an afternoon of exploration in the October sunshine included my oversized cream silk shirt, off-black stovepipe jeans from Madewell and the Sarah Flint Natalie Flats in Navy. There’s something classic about this combination, but it’s not too fussy either. Having slightly mis-matched accessories of dark navy shoes and a chocolate bag, works because each of these pieces are sophisticated enough to hold their own but by wearing them together it keeps the look casual enough to be something that a local might throw on for their own day out.

After a lavender latte and sandwich at Maman, I took the subway uptown to the Metropolitan Museum of Art where I had 3pm tickets. It was the most stunning day, and after a short wait to get inside, and checking my vaccine card, I was free to explore. My favorite parts of the Met are the sculpture halls, and so I spent some time admiring the Canovas and Rodins, before heading to the iconic Sackler Wing to see the latest Costume Institute exhibit, In America: a Lexicon of Fashion. I really enjoyed the exhibit, my favorite piece displayed was this gorgeous design by Claude Kemeni. Then I spent some time wandering the decorative arts sections of the Met, stumbling across beautiful stained glass pieces. From there I left the Met and decided to stroll through Central Park on my way back to the hotel, past the boathouse and lake. It was still quite green in the park but there were some leaves scattered underfoot, and music playing by the Bethesda Foundation, so I was happy.

Outfit 3- for my dear friend’s birthday soiree was a black and floral number from Rent the Runway. I love the bell sleeves and asymmetrical hem. I wore with heeled black booties with a square toe, to provide a little edge against a pretty feminine dress. This dress looked fancy but was actually fairly practical for the rainy weather and cooling temperatures, which is key for NYC in fall. And it was comfy so I could eat all the pizza and cake and sip on all the champagne I liked.

Sunday brunch plans encouraged me to get out of the fluffy hotel robe the next morning. For outfit 4- I wore a black faux leather shirt dress from Peter Som Collective x Rent the Runway, my tan boots and brown croco bag to meet my friend down on MacDougal St for eggs, za’atar fries, coffee and orange juice on Shuka’s patio. We took a spin around Soho, ducking into Sezane and a few other stores but the chilly wind and some lingering wine headaches had us taking the subway back uptown for afternoon naps.

In the late afternoon, after some time with my books and face-timing my sisters, I cozied up for a few hours of wandering the West Village before dinner with friends. I knew we would be eating outside and I was determined not to freeze once the sun went down. Outfit 5 was mom jeans again, brown boots, an oatmeal button down cardigan, topped off with my tweed blazer and a tan hat. Maybe it’s my mother’s advice finally sticking with me after twenty four years but wearing a hat is so helpful in staying warm and chic. As I passed through Madam Vatou’s vintage shop, Washington Square Park, I kept admiring the beautiful buildings and fascinating people I passed. On my way to meet my friends for dinner I popped into Bloomingdales and snagged a gorgeous navy cashmere pullover for sale. Dinner was on the candlelit corner of La Mercerie, one of Ina Garten’s favorite New York restaurants and it didn’t disappoint. Chicken, potatoes dauphinoise and profiteroles for dessert. If you’re looking for a special meal on your stay in New York, I highly recommend!

Outfit 6 to say adieu to Manhattan, pack up my things, snag a coffee from the Evelyn’s lobby cafe and hop on the Acela back to Washington DC needed to be cozy for the New York morning but layered so I wouldn’t start sweating when I got home. I styled the navy pullover from Aqua with the off-black cropped jeans, and black boots for a comfy but sophisticated look. I also needed to be presentable as I was working remote from the train and I feel more productive in real clothes vs. leggings which make me want to curl up and read a book or watch videos on my phone.

Looking back at these photos has me scheming for another trip already, perhaps I’ll have to head back in a few months to style a New Yorker in Spring lookbook! Now there’s an idea…



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