Okay, so I spent last week basically becoming a professional creeper in the name of “research.” I’m talking about posting up outside fancy coffee shops in SoHo, pretending to check my phone while actually photographing strangers’ outfits, and following well-dressed women for three blocks to see where they got their coats. It sounds unhinged when I put it like that, but I swear I had good intentions – I needed to figure out what actual stylish New Yorkers wear when it’s freezing but they still want to look like they have their lives together.
The thing is, working in finance means I’m surrounded by people who think “creative dressing” means wearing a navy blazer instead of black. Don’t get me wrong, I love my colleagues, but when it comes to fashion inspiration, they’re about as helpful as a screen door on a submarine. So when I have time off, I become obsessed with how other women – especially those who work in more creative fields – navigate the whole “look chic while not dying of hypothermia” challenge that is winter in New York.
I started in SoHo because honestly, that’s where the most interesting fashion happens, even if half of it is completely unwearable for us normal humans with normal jobs and normal budgets. But here’s what I noticed – even the most avant-garde dressers have figured out this layering formula that actually makes sense. I watched this woman outside the Marc Jacobs store (she was definitely not shopping there based on how long she spent looking at one bag through the window) who had on what looked like a silk slip dress, a chunky cream cardigan, a long wool coat that hit mid-calf, and these incredible knee-high boots that I’m pretty sure cost more than my monthly MetroCard budget.
The genius part wasn’t any individual piece – it was how she’d created these layers that could be peeled off as needed. Coat comes off when you’re inside, cardigan comes off if you’re somewhere warm, but you still look intentional at every stage. I tried to replicate this the next day with a midi dress, blazer, and my trusty Uniqlo heat tech underneath, and honestly? It worked better than my usual “throw on the biggest coat I own and hope for the best” strategy.
What really struck me was how different the approach is from what you see in fashion magazines. You know those winter style guides that are like “pair a cashmere turtleneck with wool trousers and ankle boots”? That’s fine for someone who goes from heated car to heated office, but what about those of us who walk twenty minutes to the subway, stand on freezing platforms, and then have to look professional for eight hours without looking like we just survived a polar expedition?
I spent Tuesday morning at the Union Square farmers market – not for vegetables, obviously, it’s winter and everything looks sad – but because I figured people there would be dressed for actual cold weather while still caring about style. This one woman caught my attention immediately because she was wearing what appeared to be a very chic uniform. Black jeans that fit perfectly, ankle boots with a slight heel, a black turtleneck, and then the most beautiful camel coat I’ve ever seen in person. Simple, right? But then she had this incredible scarf – not just thrown on but actually styled, with one end longer than the other and the whole thing positioned so it created this elegant drape.
I worked up the courage to ask her about her outfit (I know, I know, I’m becoming that person who talks to strangers about their clothes), and she told me she’s basically been wearing some version of this same formula for three years. “I invested in really good basics in colors that work together, and then I just change up the accessories,” she said. “The scarf was expensive but I wear it constantly, so the cost per wear is probably like fifty cents at this point.”
That got me thinking about my own winter wardrobe, which tends to be a collection of random pieces I’ve accumulated over the years without much thought to how they work together. I have a down coat that makes me look like the Michelin Man, several blazers that are too light for actual cold weather, and about fifteen scarves that I never wear because I can’t figure out how to make them look intentional rather than like I just wrapped a blanket around my neck.
So I decided to try an experiment. Instead of my usual approach of buying whatever catches my eye and hoping it works with stuff I already own, I’d think about building a winter capsule based on what I was seeing on the street. The most stylish women seemed to have a few things in common: they weren’t trying to reinvent the wheel every day, they’d invested in outerwear that actually fit properly, and they’d figured out the art of interesting accessories.
The coat thing was a revelation for me. I’d been buying coats the same way I buy everything else – based on price and whether I like it in the store. But watching how the best-dressed women moved through the city, I realized a good coat isn’t just about warmth, it’s about silhouette. That perfect camel coat woman looked elegant even when she was speed-walking to catch the subway. My puffy coat makes me look like I’m preparing for an arctic expedition.
I ended up spending way too much money at COS last weekend on a wool coat that actually fits properly – nips in at the waist, hits at the right length, makes me look like a grown-up instead of a college student who grabbed the first warm thing from her closet. The price made me slightly nauseous, but then I calculated how often I wear outerwear during New York winters and decided it was an investment in not looking like a homeless person for five months out of the year.
The scarf situation required more research. I watched YouTube tutorials, practiced in my mirror (yes, really), and finally figured out that the key is proportion. If you’re wearing a fitted coat, you can do a bigger, more voluminous scarf. If your coat is oversized, keep the scarf sleeker. It’s not rocket science, but apparently it’s something I needed to learn at age thirty-whatever instead of figuring out in college like a normal person.
What surprised me most was how much the footwear matters, and how wrong I’d been getting it. I’d been defaulting to my most practical boots – warm, waterproof, completely devoid of style – and wondering why my outfits looked so boring. But the women I was admiring were wearing boots that clearly weren’t chosen for their snow-trudging capabilities. They were choosing style first and dealing with the practical stuff through other means – better socks, foot warmers, strategic route planning to minimize sidewalk time.
I’m not saying anyone should sacrifice their feet for fashion, but I realized I’d swung too far in the practical direction. There’s middle ground between stilettos in a blizzard and hiking boots with every outfit. I found these ankle boots at Everlane that have a small heel but are still comfortable for walking, and they instantly made every outfit look more intentional. Sometimes the difference between looking thrown together and looking stylish is literally just better shoes.
The layering piece took more trial and error. The silk-slip-dress woman had the right idea, but silk slip dresses aren’t exactly compatible with my office dress code or my budget. But I could adapt the concept – a midi skirt with tights and tall boots, a fitted long-sleeve top, a cardigan or blazer, and then my new coat over everything. Or straight-leg trousers with a thin sweater, blazer, and coat. The key is making sure each layer looks intentional on its own, so when you inevitably have to strip down to just your base layer in some overheated restaurant, you still look like you got dressed on purpose.
I’ve been testing these formulas for three weeks now, and honestly, getting dressed is so much easier when you have a system. Instead of standing in front of my closet every morning wondering how to not look like a bag lady, I just pick a version of my winter uniform and go. It’s boring in the best possible way – boring like having a signature cocktail or knowing what to order at every type of restaurant.
The funny thing is, having a more streamlined approach to winter dressing has made me more creative with the details. When your base outfit is sorted, you can experiment with different jewelry, switch up your bag, try a bold lip color, play with how you do your hair. All those little touches that actually make an outfit interesting but that I never had mental energy for when I was struggling with the basics.
I’m sure by next winter I’ll be sick of my formula and ready to completely reinvent my cold-weather style, but for now, I’m just grateful to have figured out how to leave my apartment looking like a functional adult human instead of someone who grabbed random items from her closet in the dark. Small victories, you know?
By day, Jasmine works in finance. By night, she writes about making corporate fashion actually interesting. Her Boston wardrobe proves office-appropriate doesn’t have to mean boring, and that investment dressing can be both powerful and personal.
