What Not to Wear in NYC, According to a Shopping Writer

If you watch any movies set in New York City, you’re likely to see fashionable women dressed in extravagant, sophisticated clothing. While these movies accurately depict New Yorkers’ elevated style, they fall short in other ways: you won’t see residents strutting the city streets in stilettos or letting their miniskirts blow up while walking over the subway grate. When you have to walk extensively and rely on public transportation, practicality is crucial. So, when I see someone make these fashion mistakes, I usually assume they’re a tourist. 

After living in NYC for two years, I’ve swapped out most of my impractical, uncomfortable clothes and shoes for functional pieces that are just as stylish. If you’re shopping for an upcoming New York trip or hoping to look more like an NYC local, keep reading for the eight fashion faux pas you don’t want to make—and the wardrobe essentials to buy instead. Shop stylish sandals, comfy jeans, and walking shoes, starting at just $20 at Amazon. 

Don’t: Wear Flip-flops

Do: Wear Platform Sandals

As much as I hate when people complain about New York being dirty, it’s true. The streets are covered in urine (dog or otherwise), and the subways are filled with unpleasant surprises. That being said, it’s probably not the best idea to wear flat flip-flops—unless you plan on giving your feet spa-level exfoliation at the end of the day. 

While some New Yorkers would opt not to wear open-toed shoes at all, I think platform sandals are okay, since they keep your feet a bit further away from the street. This will help keep your feet clean as you explore the city (although I still recommend a scrub before getting into bed). I love this nostalgic pair from Steve Madden, which is stylish and comfortable enough to “walk all day long.”

Don’t: Wear Miniskirts

Do: Wear Skorts

When your average day involves going up and down subway stairs, walking through wind tunnels, and stepping over breezy grates, it’s best not to wear miniskirts that can easily expose you. I often see New Yorkers opting for skorts instead, and the sporty style is so trendy right now, too. This skort is a steal at just $20, and it has over 4,900 five-star ratings. Reviewers love its sweat-wicking material, all-day comfort, and the hidden pocket sewn into the shorts. 

Don’t: Wear Short Dresses

Do: Wear Maxi Dresses

Another solution to blowing hemlines? Maxi dresses. I spot this style every single day living in NYC, and now my closet is overflowing with them. A flowy maxi dress is the most comfortable style for spring and summer, and it will keep you securely covered all day long. I love that this tiered dress can be paired with sneakers or heels depending on the occasion, and reviewers rave that it’s flattering on a variety of body types. One size-14 shopper wrote that it “complements the curves without being too revealing.”

Don’t: Travel Light

Do: Be Prepared With a Spacious Tote

We frequently recommend belt bags at Travel + Leisure, but if you’re hoping to look like an NYC local, you should pack a spacious tote instead, filled with daily necessities. My bag always includes hand sanitizer, my favorite sunglasses, and a water bottle—plus a handheld fan in the warmer months (trust me, you’ll need it on the train). Needless to say, a small bag isn’t going to cut it. Plus, stores charge for bags, so toss new purchases in your tote instead. 

This one has a laid-back, trendy design, plus “so much room” for the day’s essentials. This brown version is classic, although I also love the bold green and burgundy colors.  

Don’t: Wear Stilettos While Commuting

Do: Keep the Heels in Your Bag

You might expect New York to be crawling with powerful women in stilettos, but the truth is, New Yorkers are much too practical to walk the city streets in heels. Instead, commuters wear comfortable flats around town and change into heels once they arrive at their destination.  

One reviewer wore these flats all day while running errands and raved that they “felt like sneakers.” I love the trendy bow detailing on the toe, plus they fold down to take up less space in your tote bag or carry-on. 

Don’t: Wear White Sneakers

Do: Wear Darker-colored Sneakers

While plenty of New Yorkers wear white sneakers, I got tired of finding dark spots and stains on my shoes at the end of the day. Instead, I wear black and colorful sneakers that hide dirty spots more easily. Now, I can walk through Central Park (or even Times Square) without worrying about staining my shoes. 

These New Balance shoes will stay new-looking for longer thanks to their all-black upper. One shopper brought these walking shoes on a trip to NYC and raved that it felt as though they were walking on “clouds,” so they didn’t experience any pain after hours of walking. 

Don’t: Wear Tight Jeans

Do: Opt for Stretchy Fabrics

Nothing beats the look of classic denim, but it’s simply too uncomfortable to wear during long days in NYC. The stiff feel, plus the suffocating heat of summer in NYC, is a recipe for disaster. That’s why I’ve swapped out my tight, denim jeans for more comfortable styles that are better suited for all-day wear. 

I love the look of this wide-leg pair that comes in blue, black, and even pink shades—but this white color is my favorite for the season. With two percent elastane and an airy, wide-leg silhouette, these are the “most comfortable jeans” one shopper has ever owned. 

Don’t: Forget to Layer

Do: Bring a Versatile Button-up

The fluctuating temperature in NYC is enough to give you whiplash. You’ll be chilly one minute and sweating in a subway station the next, which is why I always bring a button-down or sweater along with me just in case. Not only do I use this extra layer to keep me warm when the sun sets, but I also lay it down on subway seats if I’m wearing shorts or a dress.

A white button-up goes with just about anything, and this Zeagoo option is made of 100-percent cotton, so it will be breathable enough for the warm months. 

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