20 Street Style NYC Winter Outfit Ideas 2026

I just got back from New York during winter and wow, the outfits were next-level. Somehow, even in the freezing cold, everyone looked so effortlessly put together. I found myself mentally bookmarking every look I saw, trying to figure out how they pull it off so well.

You know that cool, classic NYC style that feels so natural? I cracked the code and trust me, you’re going to want to copy these looks. These ideas totally work for any chilly city, especially if you’re planning a New York trip soon.

Below are all the New York winter outfit combos I’m obsessed with right now. I have a feeling you’re going to fall for them too.

Mastering the Art of Layering

If there’s one thing that changed the way I dress for winter, it’s layering. It makes your wardrobe feel so much bigger because you can get creative with pieces from other seasons. I love layering turtlenecks under lighter button-downs or even repurposing summer dresses by styling them over fitted knits. It’s practical and gives your outfit a more styled feel. Plus, it’s a great way to stay warm without piling on just one bulky piece.

Brown Leather Winter Jacket with Faux Fur + Baggy Jeans + Uggs

Faux fur collars on leather jackets just give off that rich, cozy vibe. You’ll feel like a million bucks walking through Soho, even if you’re just popping into Trader Joe’s. Baggy jeans and Uggs have basically become the unofficial winter uniform in NYC because it’s that sweet spot between comfortable and put together.

Invest in a Faux Fur Jacket and Tights

Not many people would dare wear denim shorts in the middle of winter, but Suki Waterhouse pulls it off with pure rockstar energy. The secret to making it work? A bold faux fur jacket layered over a textured long-sleeve top. Pair it with sheer-effect thermal tights and cowboy boots for that cozy-but-edgy feel. Add slim oval sunglasses for a retro flair. It’s giving Daisy Jones in the best way possible.

Dark Navy Jean Jacket + Black Mini Skirt + Leg-Warmers

Leg-warmers are back and honestly it’s fun even if they’re not the most practical with boots. Rocking a mini skirt in NYC during winter is bold, but the leg-warmers kind of bridge that gap between fashion and not freezing. It’s that cute-meets-courageous energy that really works when styled right.

Brown Knit Cardigan + Straight-Leg Navy Jeans + Cream Knit Scarf

The combo of brown and navy always feels expensive and elevated, even if it’s super simple. It’s richer than the typical all-black look but still neutral enough to mix and match. The cream scarf ties everything together perfectly and you can wrap it a bunch of different ways depending on just how cold it gets outside.

Invest in a Timeless Winter Coat

Even though I seriously can’t stand New York winters, I have to admit that winter fashion is one of the few things that gets me excited when the temps start to drop. A high-quality winter coat is one of those pieces that truly lasts season after season. Over my eight winters in the city, I’ve slowly built a collection of coats I’m proud of. The key is choosing styles in a neutral color palette so they stay timeless. Even if your budget is tight, a good coat doesn’t need to break the bank. Focus on fit and classic shades, and you’ll find yourself reaching for it every year.

Uggs + Faux Fur Jacket + Baggy Jeans + Grey Scarf

Throwing on a faux fur jacket instantly makes any winter outfit feel a little more glam, even if you’re just running errands in the Financial District. The grey scarf adds that effortless chic vibe, and once you try this combo, there’s a good chance you’ll live in it. Jess wears a similar look nonstop from December to March because it just works for everything from coffee runs to dinner plans.

Adidas Samba + Baggy Jeans + Black Wool Coat + Turtleneck Longsleeve

Sambas are literally everywhere in NYC right now and they’re actually a solid winter shoe option since the grip is better than most cute sneakers. A black wool coat is a must-have investment that goes with everything, and a simple turtleneck layered underneath keeps things warm without looking bulky. This whole look is stylish without even trying.

Layer, Layer, Layer

What’s more New York than a pair of Timberlands? Honestly, not much. Emily Ratajkowski nailed that city-cool vibe with her Mango striped cardigan sweater that came with a built-in scarf, and though it’s sold out in a lot of sizes, the outfit formula is easy to recreate. Her Gap jacket is still available and totally wearable for winter layering. Pair it with oil-wash pants and a solid pair of boots, and you’ve got an outfit that’s just as practical as it is stylish. Don’t forget bold sunglasses and statement hoops to finish the look.

Blue Knit Cardigan + Black Suit Pants + White T-Shirt

Blue cardigans are seriously underrated when it comes to planning New York winter outfits. They bring in just the right pop of color while still keeping things polished. In a sea of black, this little bit of blue stands out without trying too hard. Suit pants are surprisingly warm and honestly so much more comfortable than jeans, especially when you’re stuck on a delayed train for forty minutes.

Elevate Casual Staples With Leather

After watching Nosferatu, something shifted, and ever since, Lily-Rose Depp’s casual style has been on my radar. Her Y2K-inspired Chanel bag is definitely wish-list material, but the real charm of her outfit is how she turns basics into fashion moments. A faux leather jacket layered over a striped turtleneck feels effortless but pulled together. Add relaxed-fit jeans, cozy ribbed socks, and sleek loafers for that laid-back downtown vibe. Her mini top-handle bag adds the perfect finishing touch.

Double Down on Denim

Bella Hadid gave us a major throwback moment when she stepped out in a denim skirt set from Roberto Cavalli’s 2002 collection. While the exact set is tricky to find, the denim-on-denim inspiration is totally doable. A fitted denim jacket with a midi-length denim dress creates that cool, vintage feel. She styled it with structured knee-high leather boots and a roomy shoulder bag. The best part? Her sunglasses are still in stock and super affordable. It’s a full denim look that’s bold and unexpectedly chic.

Brown Wool Coat + Black Baggy Jeans + Black Longsleeve

A brown wool coat really pops in a crowd of black jackets, especially during rush hour when everyone looks the same. The black baggy jeans are perfect for longer commutes since they’re comfy and hold up well through a full day. The overall outfit hits that effortless, put-together winter vibe you always see on the streets of New York.

Tailor Your Look to Perfection

Brooke Shields proved she’s still a style icon with her sharp, tailored suit look. A fitted blazer over a crisp collared shirt and classic trousers is such a power move. Metallic heels add that little touch of drama, while her slim tie brings in a playful, polished edge. Throw in oversized frames to channel that confident, cool energy. This look is all about clean lines and attention to detail, perfect for making a statement even when it’s freezing outside.

Tailored Pants for Easy Chic

Tailored trousers have become one of my favorite winter go-tos when I want to feel polished but still comfy. While they’re not super warm on their own, the fit allows enough room to slip on thermal underlayers underneath. One trend I’ve been loving lately is pairing chunky UGG boots with trousers. It’s the perfect combo of cozy and cool, and it totally works for a practical winter day out in the city.

Brown Leather Jacket + Wide-Leg Jeans + Leopard-Print Scarf

Leopard print scarves are having such a moment right now. They’re ideal for planning winter outfits in New York because they add a little personality without going over the top. A brown leather jacket totally fits the NYC vibe since it’s sturdy enough for the streets but still looks polished for wherever you’re heading. Wide-leg jeans are a win because they’re comfortable for all that subway sitting and the surprise walks you’ll definitely find yourself doing.

White Teddy Jacket + Black Leggings + Platform Uggs

Teddy jackets honestly feel like a warm hug, and pairing them with platform Uggs is such a smart move when you’re dealing with icy sidewalks. This look gives you that cute, cozy vibe while actually being wearable for city winter weather. It’s basically the ultimate combo for staying comfy without sacrificing style.

The Winter Boot Lineup

Boots are hands down my favorite part of winter dressing. Trends come and go, but I always stick to silhouettes that feel classic and versatile. Chelsea boots, cowboy styles, simple neutral combat boots, mid-calf rain boots, and ankle-length staples are all part of my collection. I also never skip UGGs when I want something that’s both cozy and city-appropriate. Choosing quality, neutral-toned pairs means they’ll go with everything and hold up through tough winters.

Black Leather Jacket + Dark Grey Baggy Jeans + Black Cardigan

Layering a cardigan under a leather jacket is such a clever trick for cold-weather outfits in New York. It keeps you warm without looking bulky and adds just enough detail to make the outfit feel intentional. Dark grey baggy jeans are a game changer because they hide all the salt stains and slush marks better than black does. You’ll totally get it after one walk through the city in winter.