So there I was last Tuesday, balanced on one foot trying to get a shot of this woman’s incredible layered look on Bedford Ave, when I nearly got taken out by a delivery guy on an e-bike. God, the things I do for street style documentation. “Sorry!” I yelled after him, though honestly it was totally my fault for practically standing in the bike lane. The woman with the fantastic oversized menswear blazer over a sheer dress just laughed and asked if I needed her to pose again. This, my friends, is the difference between fashion people and normal humans—fashion people understand that sometimes you need to risk life and limb to capture the perfect outfit.
I’ve been stalking the streets of New York like some kind of style anthropologist for the past three weeks, cataloging the shift from late summer desperation (“I refuse to acknowledge fall is coming”) to early autumn experimentation (“Maybe I can still make this work with a cardigan?”). And let me tell you, the city is serving LOOKS right now. Like, capital-L LOOKS that make me want to go home and set fire to my entire wardrobe and start over.
New York has always been a battlefield of personal style—it’s literally impossible to shock anyone here. You could walk down the street in nothing but a shower curtain and platform crocs, and New Yorkers would just step around you like, “Excuse me, I’m late for my therapy appointment.” But even in this anything-goes environment, there are clear patterns emerging, neighborhoods each with their distinctive fashion fingerprints that tell you exactly where you are without checking your phone.
SoHo, predictably, is luxury minimalism central right now. I spent a rainy Thursday camped out at that overpriced coffee shop on the corner of Prince and Mercer (you know the one—$7 for an oat milk latte in a cup roughly the size of a thimble) just watching the parade. The interesting thing happening is this tension between the ultra-sleek, “I have an art gallery and you’re not cool enough to visit it” aesthetic and something much more playful that’s bubbling up underneath.
Take this one woman I spotted—easily 5’11”, hair slicked back in that wet-look style that I’ve tried approximately 42 times and always end up looking like I just got caught in a downpour instead. She was wearing what was essentially a man’s suit in this delicious chocolate brown color, tailored within an inch of its life, no shirt underneath, just a simple gold pendant necklace. Classic SoHo rich-person uniform, right? But then—and this is what made me nearly spill my ridiculous coffee—she had these electric blue socks showing beneath the slightly cropped pants and was wearing what I’m almost positive were those Balenciaga Crocs platforms. The $850 ones. With a suit. And somehow it WORKED.
I caught up with her (okay fine, I basically chased her down the street like a weirdo) and learned her name was Alessandra, she works in “creative direction” (which could mean literally anything in this city), and the suit was actually vintage Armani that she had tailored. “I like fucking with proportions,” she told me, which is possibly the most SoHo thing anyone has ever said to me. Alessandra, if you’re reading this, I’m still thinking about those socks.
Over in Williamsburg—my home turf—the vibe is, as always, trying very hard to look like we’re not trying at all. The Bedford Ave L train stop continues to be the best free fashion show in the city, especially around 6 PM when everyone’s heading home from their mysterious creative jobs that somehow fund $3,200/month one-bedroom apartments.
The big thing I’m seeing is this almost aggressive return to early 2000s silhouettes, but make it sustainable. Low-rise everything, but it’s deadstock denim or upcycled vintage. Tiny shrunken cardigans that look like they’ve been “borrowed” from a small child, paired with massive wide-leg jeans that pool around chunky boots. So many belly chains I’m having traumatic flashbacks to my junior high fashion disasters.
This girl Jamie I spotted was wearing the perfect example—low-rise cargo pants (yes, CARGO PANTS, we are fully back in 2003) that she’d thrifted and then hand-embroidered with these tiny abstract shapes down one leg. She’d paired them with a cropped white ribbed tank, an oversized denim jacket that had belonged to her dad in the ’90s, those chunky Fila Disruptor sneakers that refuse to die, and at least fifteen delicate gold necklaces of varying lengths. Her hair was in that messy half-up style with two little face-framing pieces that the TikTok girls have been doing to death. It shouldn’t have worked—it was literally about seven trends happening simultaneously—but on her, it was magic.
“I just wear whatever makes me happy,” she told me, which is what literally everyone in Williamsburg says while secretly having spent three hours planning their outfit to look perfectly thrown-together. I know this because I do it too. We’re all liars here.
The Lower East Side is where things get really weird and wonderful right now. If SoHo is polished luxury and Williamsburg is studied casualness, the LES is pure fashion chaos energy. It’s like everyone collectively decided that post-pandemic, life is too short not to dress like the main character in your own deranged movie.
I spent a Saturday night bopping between a few spots on Orchard and Ludlow, and it was like watching fashion kids playing dress-up with exactly zero rules. Massive platform boots that add a solid foot of height. Vintage nightgowns worn as dresses with combat boots. Sheer everything. Gender? Never heard of her. The coolest people were mixing decades with abandon—’70s disco tops with ’90s raver pants and Y2K accessories, all somehow held together by pure confidence.
This one guy—well, I think he identified as a guy, I didn’t ask and it doesn’t matter—was wearing what appeared to be a 1950s prom dress, cut short at the front, with basketball shorts underneath, knee-high white boots, and a trucker hat. It was giving “fashion fever dream” and I mean that as the highest compliment. When I asked to take his picture, he struck three poses in rapid succession like he’d been waiting his whole life for this moment, and honestly, he deserved his runway.
So what are the actual trends you can adapt without looking like you’re trying to be 23 when you’re firmly in your 30s like me? (Not that there’s anything wrong with dressing however you want at any age—as my mother loves to remind me, “Harper, I wore mini skirts in my 50s and I’ll wear them in my coffin.”)
Here’s what’s worth considering, based on my highly unscientific street stalking:
First, proportions are getting weird again, thank god. After years of everything being either oversized or bodycon with no in-between, we’re seeing this amazing play with volume. Tight tops with massive pants. Huge, boxy jackets with tiny micro-shorts. The trick is to balance—if one half of you looks like you’re drowning in fabric, the other half should create some kind of silhouette so you don’t look like a walking duvet.
Emma Chen, a buyer I ran into outside Ludlow House, was wearing this incredible voluminous white shirt—so oversized it was practically a dress—with these skin-tight split-hem leggings and pointy slingback flats. “It’s all about creating tension in the silhouette,” she told me, which I immediately wrote down in my phone because it sounded smart and I’m stealing it for future use.
Second, color is back in a big way, but not in the rainbow explosion way. Think unexpected color combinations—chocolate brown with electric blue (like Alessandra’s socks), deep burgundy with tangerine, navy with acid green. New Yorkers will always love their black—myself included, as I type this wearing black jeans and a black sweater—but the coolest cats are using color in ways that feel thoughtful rather than thrown together.
This woman Diane I spotted in Washington Square Park (technically not one of my designated hunting grounds, but I was meeting a friend for coffee and couldn’t help myself) was wearing an entirely monochromatic burgundy outfit—wide-leg trousers, ribbed tank, oversized blazer, even burgundy loafers. It was simultaneously extremely simple and completely striking. When I complimented her, she just shrugged and said, “It’s easier than matching different things.” Diane, you’re a genius and I’m stealing this idea immediately.
Third—and I know this is controversial—but low-rise is happening whether we like it or not. I’ve fought it, I’ve denied it, I’ve sworn I would never again subject myself to the constant awareness of whether my underwear is showing, but here we are. The good news is 2023’s low-rise is not 2003’s low-rise. It’s more like mid-low-rise, sitting just under the belly button rather than alarmingly close to one’s… well, you know.
My advice? If you’re venturing back into low-rise territory, balance it with something oversized on top. A boxy jacket, an oversized sweater, a big shirt—something that creates proportion and doesn’t make you feel like your entire midsection is on display. And maybe do some core exercises first. (I’ve been doing Pilates once a week for three months and I’m still not convinced my abs are ready for public consumption, but that’s between me and my therapist.)
The accessories game has gone in two completely opposite directions: either extremely minimalist—thin gold chains, tiny stud earrings, simple leather bags—or completely unhinged maximalism with stacked jewelry, multiple bags at once (yes, really), and shoes that could double as architecture.
I saw a woman in the West Village wearing no fewer than four necklaces, six rings, earrings that looked like miniature wind chimes, and carrying both a structured leather shoulder bag AND a tiny beaded purse attached to her belt loop. When I asked her about it, she laughed and said, “My apartment is too small for all my stuff, so I just wear it all.” New York real estate problems turned into fashion statements—we love to see it.
The final thing worth noting—and this makes my sustainability-loving heart so happy—is that vintage and secondhand continue to reign supreme across all neighborhoods. The coolest looks I documented were almost always a mix of vintage finds, modern basics, and maybe one splurge designer item as the cherry on top.
Sophia, a graphic designer I met at a coffee shop in Greenpoint, was wearing vintage Levi’s she’d had tailored to fit perfectly, a men’s white tank top, a gorgeous oversized vintage Burberry trench that she’d scored at a consignment shop in Connecticut (“Always thrift in rich neighborhoods,” she advised wisely), and brand new Maison Margiela Tabi boots that she admitted were “the most expensive thing I’ve ever purchased besides my laptop.”
That high-low mix is quintessentially New York and always will be—the city’s too expensive to dress head-to-toe in luxury unless you’re a real estate heir or a Wall Street bro, but we’ve got too much fashion pride to go all fast fashion. The result is this beautiful collage of pieces with stories, whether it’s “I saved for six months for these boots” or “This was my grandmother’s scarf” or “I found this on the street in front of my apartment building, can you believe someone was throwing it away??”
New York street style hasn’t looked this alive, this weird, or this personal since before the pandemic. There’s a sense that people are dressing for themselves again—not for Instagram, not for some algorithm, but for the sheer joy of self-expression and the knowledge that in New York, someone like me might be lurking around the corner, ready to make them internet famous for their sartorial brilliance.
Just watch out for those delivery bikes if you’re taking pictures. They wait for no fashion moment, trust me.