I’ll never forget my first business trip to New York.
I flew in from LA. As I walked from my taxi to my hotel, a homeless man looked at my coat and said to me, “Nice. Versace circa 1980s.”
My mother grew up an hour north of Manhattan and always kept a pied-à-terre in the city. From childhood visits, I’ve always had vague memories of a stylish citizenry.
A homeless guy IDing my vintage jacket though? Truly, New Yorkers are a sartorially remarkable group.
Today, after years of living here, I know that dressing like a New Yorker means a lot of things to a lot of people. And, it can take time to achieve.
But, I also learned some effective practices that can get you there fast and efficiently. New Yorkers love efficiency, after all.
Find Where and How You Best Fit into New York’s Many Subcultures
New York is one of the most diverse places in the world. This is a city where you’ll find the most conservative, stiff-upper-lip, legacy-only women’s club on the same block as the local swingers sex dungeon.
So, my first piece of advice is to find what kind of New Yorker you are. Or at least start to figure it out, and do it with intention.
Yes, categorically connecting a specific style to a specific neighborhood is effectively stereotyping. If you’re a beginner to New York fashion though, it’s not a bad place to start.
Are you a wheeling-and-dealing Wall Streeter? An old-world Park Avenue legacy? Perhaps you’re a hip and creative Harlem or Bushwick type.
It’s often said the West Village and East Village are uniquely fashion forward, though the former is sleeker while the latter is more eclectic.
Speaking of eclectic, maybe you’re a mix of different styles. Or maybe your weekday self identifies with a more put-together look, while weekend you fancies something more unconventional.
This is the part that takes the most research and understanding. However, it doesn’t take long to start somewhere and commit.
“Sleekify” Your Personal Style, Starting with Your Watch and Shoes
Once you’ve committed to your New York aesthetic, you’re going to level it up. The idea of the “sleek” New Yorker is definitely a stereotype that doesn’t apply to everyone. But, it’s a good shorthand to communicate your connection to the city.
The way I’ve been told to do this is to take your personal style, and make it look like the version of that person who holds a position of power in their career.
So if you’re going for an artsy, boho look, dress like the hottest, latest artist who runs his own studio in Brooklyn. If you’re going for a traditional, white collar look, dress like the CEO who takes his black car from his Tribeca or Upper East Side townhouse to his office in Midtown.
There’s different ways to do this, but where you should start is with your watch and your shoes. Invest in a good timepiece and make sure your shoes are high-quality. No matter how casual or quickly put-together your outfit is, a nice watch and shoes will bring an effortless chicness to your look.
This doesn’t necessarily mean going for a Rolex and some Bottegas. Fortunately, there are good watches and good shoes in every price range. Do your due-diligence and stay within your budget and within the style you’ve adopted.
A Brooklyn hipster might be wearing a limited edition Seiko in an unconventional color, with some quality leather sneakers.
A fashion-forward guy (dressing like he’s the editor of GQ) might wear a Rolex. Or, he might wear something with cool factor and pizazz, like the Citizen Promaster Nighthawk or a Hamilton Ventura.
Citizen is your go-to brand if you love complicated dials and technical marvels. If you want a rugged and supremely functional token of horological history, check out the Promaster Nighthawk.
If you are going for an old money, uptown look though, check out secondary markets for vintage Rolex, Omegas, and Pateks. Then find some welted full-grain leather loafers.
No matter how casual you are, wear your nice shoes and watch everywhere you go.
Be Ahead of Trends—but Don’t Necessarily Follow Them
An important reason to know the trends isn’t to follow them necessarily, but to avoid the polar opposite of them. For example, if oversized clothes are trending, you don’t necessarily have to comply, but you should definitely avoid skinny fits.
It’s okay not to look trendy. It’s not okay to look irrelevant.
Subscribe to finger-on-the-pulse fashion newsletters and keep tabs on what’s being shown during Fashion Weeks in different cities.
The Big Four are Paris Fashion Week, New York Fashion Week, Milan, and London. Paris is the most important, followed closely by New York. They happen twice a year in February and September.
And if you do love trends, don’t just blindly follow.
They may make sense in your everyday style, or they may make sense in certain parts of your life.
For example, at the time of this writing, we’re deep into last year’s oversized clothing trend.
My boss would absolutely have words with me if I showed up to work in an oversized suit. Still, I can wear oversized linen trousers in beige with a knit polo during a warm weekend.
If you aren’t a trendy guy, but want to experiment a bit, you can find subtle ways to incorporate trends.
Take a flowy, regular fit pair of trousers, hemmed so they maintain straight lines and don’t bunch up. When worn, it registers as following the oversized trend, but it looks cleaner and more grown-up.
Brand Names Aren’t Necessary, but They Help
Fashion with a capital F and luxury are a natural part of New York’s ecosystem.
The thing no one mentions is that this isn’t always because everyone is trying to flex via fashion. It’s because these luxury brands are literally headquartered in this city. They’re a physical part of our lives.
My good friend grew up in Manhattan, and never considered himself a fashion guy. However, for work, he spent a year in Chicago and realized he simply wasn’t a fashion guy by New York standards.
Fortunately, there are high-end brands and well-respected brands for every personal style.
The traditional guy has his Brooks Brothers, Ralph Lauren, and Burberry—at least, their core lines. The fashion-forward guy has his Balenciaga and McQueen. Goths and rockers can turn to Rick Owens.
My best advice when it comes to incorporating a big-name brand into your wardrobe is to go for a garment you don’t need several multiples of and can be worn with a wide range of outfits. A trench coat, a scarf, or a blazer are all good examples.
Then, sift through your local vintage shop or your eBays and RealReals, and see if you can find a good deal.
Always Dress with Intention
Dress the part. Going to a black-tie gala? Wear a full tuxedo with a bowtie and throw a waistcoat in there. A networking event? Go for a full power suit, cufflinks and all. Off to a warehouse party? Get some neons and wild accessories going.
Regardless, you want to commit hard to your look.
If you go minimalist, go chic minimalist. Think two colors max, with simple, and clean lines. In fact, this might be one of the tentpole New York looks. Try a navy or black cashmere turtleneck with tonal trousers and Chelseas, with an unbuttoned peacoat in another color like camel or charcoal.
If you want to be unconventional, be creative and fearless. A friend of mine, a fashion designer, once arrived at a gala wearing a mesh scoopneck embroidered with decorative florals with a pinstripe suit. Yes. Mesh. As in exposed chest and stomach. He was a huge hit.
Another way to dress with intention is to make sure at least one of the garments on your person is expressly unique. And this doesn’t necessarily mean trying to find something wildly unconventional to incorporate into your combination.
For example, the hypothetical minimalist outfit I described features one unique item, and that’s the coat. It’s the one piece that isn’t tonal with the rest of the outfit.
You can also go for something so vintage, people don’t often see it anymore. Examples include an old lapel pin, an old-fashioned cape coat, or a double-breasted velvet blazer.
Be Confidently Yourself
Dress as the best, most high-quality version of yourself. This is going to require upgrades and investments, of course.
Don’t wear anything you absolutely hate just because you think it’ll make you look more New York or because it’s on-trend.
You need to have a confident, cool way about how you wear your clothes.
As Sir Hardy Amies once said, “a man should choose his clothes with intelligence, put them on with care—and then forget all about them.”
So I don’t get flack from people who were born and raised here, there truly isn’t one way to dress like a New Yorker.
To reuse a term I used earlier, these tips are simply style shorthands to give people the impression of what different types of New Yorkers are in the greater imagination.
New Yorkers are, in essence, confident and chic people. And this is reflected in the way they dress.
