Hold My Bagel: 30 Iconically Bizarre Fashion Looks That Got Spotted In NYC

"New York is a city where truly anything goes," said New Yorker, thrifter, and fashion enthusiast, Nicholas Portello, to Bored Panda.

"Of course, the type of style can often depend on where in the city you are. For example, Brooklyn is known for its more colorful and experimental street style. The Upper East Side is known for more thoughtful tailoring and more upscale posh fashion. These boundaries aren’t exclusive but are good indicators. The city is nothing if not creative, and people from every area have their own innovative and exciting personal style," he explained.

During Fashion Week, Nicholas tells us that locals love going out even more and wearing things they may have been saving to make a strong impression. "There are countless events, dinners, and brand pop-ups each day of Fashion Week, so attendees must dress to impress!"

"New Yorkers have a really cool and unique sense of style, inspired by its melting pot culture," says fashion expert and the author of The Encyclopedia of New York Fashion, Jewel Elizabeth. "It’s all about mixing things up—high fashion with laid-back vibes. You’ll see everything from stylish sneakers to chic winter coats, and each neighborhood has its own unique feel."

"New Yorkers literally wear their personality on their sleeves, with plenty of bright colors, bold patterns, and, of course, New York inventions like the baseball cap and puffer coat. In NYC, we walk everywhere, so it’s about looking while working long hours and dressing for function, whether in the boardroom or on the subway every day. NYC fashion is relaxed but confident, making the streets feel like one big, lively runway."

Nicholas' favorite thing about fashion in New York is that people don't shy away from going all out and dressing like themselves.

"It seems like every time I’m walking somewhere in the street, I see an article of clothing or outfit that excites me. There is always something interesting going on in New York. It’s where Julia Fox can wear a purse filled with Velveeta (a brand of manufactured cheese) and Paul Mescal can make headlines for picking up a Sweetgreen salad in short shorts. The city is truly a runway," he fondly said.

What Jewel likes the most about New Yorkers' style is the diversity and creativity. "The city is a melting pot of cultures, which means that everyone's personal style is influenced by their unique backgrounds and experiences. We take chances! Fashion in New York is always evolving, whether it's the high-energy atmosphere during Fashion Week or the cutting-edge designs you might see out in Bushwick or Harlem, there's always something fresh and exciting happening, and we're not afraid to try it!"

Naturally, we couldn't let the fashion enthusiasts go without asking for some fashion advice for those who are planning to visit New York and want to fit in with the locals.

"If you’re visiting New York, I recommend you take a risk with fashion!" says Nicholas. "Wear something you may feel a bit shy to wear at home. Wear something with an exciting story that makes you feel good. There is a stereotype that New Yorkers aren’t kind people—I don’t find this to be true. We are curious fashion lovers who want to learn more about people from around the world! Just go for it and don’t look back—the city is yours to make an outstanding impression in!"

"Go with the season and wear something bold," agrees Jewel. "Of course, a Yankee's hat will always work and the all-black aesthetic is signature NYC. However, locals also wear bold colors, mix high-end and budget items, and make sure they have a Metrocard."

Another rule of dressing like a New Yorker is wearing black. Yep, you heard that right—black. Even though it might seem like the most uninteresting color ever, the locals frequently sport it because it's functional and fashionable.

Black clothing looks good in any circumstance or situation. It hides stains, sweat, snow, salt, and any sticky stuff a person might sit in in the subway. Dark tones can also be paired with just about anything from jeans to high heels for nearly every social occasion. In fact, the Fashion Institute of Technology, which is a big deal, has announced black as an unofficial fashion palette for New Yorkers since the ‘70s. 

In the fast-paced and unpredictable New York, locals have to be prepared for their happy hour to turn into an unexpected party, bar hopping, or gallery visit. Black pieces can be styled into sharp, intelligent, and one-of-a-kind outfits. Even though the color seems basic, having dark clothing items that are flattering can provide people with a great canvas that could be added on. The pieces could include tailored pants, quality leather jackets, ankle boots with gold accents, skirts, and bags.

For anyone traveling to New York, neutral black and dark grey pieces can create a great travel capsule wardrobe. Packing a few black or grey shirts and pants that fit well will prepare visitors for anything that the city throws at them. 

“New Yorkers have a way of using basic pieces to create fashion-forward outfits,” writes Travel Fashion Girl. “Well-tailored t-shirts in neutral colors, a great-fitting pair of jeans, a crisp button-down t-shirt, and trendy sneakers are all staples in any New Yorkers closet! You can never go wrong if you stick to the basics.”

That said, New Yorkers still love a pop of color and weirdness. A nice scarf, bright sneakers, leopard-print bag, or zebra-print belt can stand out even more against the canvas of black. Interestingly, neighborhoods like Williamsburg, Long Island City, Greenpoint, Red Hook, and Bushwick are known to be almost comically colorful.

While thinking about the style and colors, it’s also important to not forget comfort. Since New Yorkers walk a lot, snug and fashionable shoes are of the utmost importance. Unfortunately, old, scuffed, faded hiking boots or gym shoes aren’t going to pass, as they scream ‘tourist’ and some nicer bars refuse to let people with such footwear in. Stylish sneakers, slip-on flats, or chukka boots are a way to go. Locals notice these things so make sure to pay attention to your shoes while visiting the Big Apple.

Another factor to think about when choosing what to wear is the weather. In wintertime, it might be best to opt for lightweight yet insulating layers, like thermal layers or cashmere or merino wool sweaters instead of bulky jackets and knitted jumpers. A waterproof coat and some sturdy waterproof boots are some other major essentials, as streets quickly get slippery when it rains or snows.

Meanwhile, summer in such a big city can be very hot and humid so wearing loose and lightweight fabrics is a must. Even though the weather can go to scorching levels, avoid wearing sands and choose lightweight and protective sneakers or flats, as they’re more practical and provide safety in case you step on sharp objects. Have a lightweight jacket handy too, as microclimates like subways can get quite chilly.

Lastly, bring a backpack. Although it may seem counterintuitive, as tourists are often spotted wearing these bags, it’s not weird to carry a backpack around New York. It allows people to bring everything they will need throughout the day, as quickly heading home to change isn’t usually an option. This is great news for travelers—they can bring water bottles and extra layers without standing out.

All in all, try not to overthink it too much and enjoy playing with fashion when in New York! Thirsty for more New York oddities? Check out our previous article on all things weird and cool that happened there, or go for our piece on some of the awesome things New Yorkers have thrown away.