Strutting through the snowy streets? Discover the chicest plus size New York winter outfits to slay the season. Your guide to conquering the city in style!
On a freezing New York morning, wondering how to stay warm without losing your style? I get it – I’ve been there too.
Let me tell you about my first winter in New York as a plus size woman.
I remember stepping out of my apartment wearing what I thought was a warm outfit, only to have the wind cut right through me.
That day taught me something important: winter fashion in New York is its own art form, especially for us curvy queens.
You see, New York winters demand more than just throwing on layers.
We need outfits that work for rushing through subway stations, walking blocks to our favorite restaurants, and looking fabulous for impromptu rooftop drinks (even in December!).
The challenge? Finding pieces that keep us warm without making us look like we’re wearing a sleeping bag.
Through trial and error – and yes, some fashion disasters – I’ve discovered what really works for our bodies in this concrete jungle’s harsh winters.
That’s exactly why I’m sharing my real-world tested outfit ideas.
Must-See: Plus Size Cute Winter Outfits.
24 Plus Size New York Winter Outfits
After helping countless plus size friends transform their winter wardrobes, I know these looks work in real life, not just on Instagram.
Ready to discover how to build a winter wardrobe that makes you feel like you own these city streets?
Let’s dive into 24 plus size outfit combinations that’ll have you conquering New York winter with style and grace.
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1. Winter Gray Hooded Two-Piece Loungewear
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This loungewear set hits different in heather gray. You’re looking at a cropped hoodie with wide-leg pants that give you room to move.
Those deep pockets? They’re not just for show – they hold your phone, keys, whatever you need. This kind of sweatshirt material that feels like a hug.
The full-length pants would pair great with sneakers or boots. It’s what you want for those New York winter days when you’re running errands or chilling at home.
2. Emerald Green Zipper Track Set with White Crop Top
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This green tracksuit brings the heat to New York streets. You get a bomber-style zip jacket with clean lines and matching wide-leg pants.
The white crop underneath breaks up the color. They turn this set from gym gear to street style. Peep the details – front zip lets you control your vibe.
This set works for brunch, shopping, or just flexing around the city. It’s comfort meets class, no questions asked.
3. Boss Babe Black Two-Piece Suit with Glitter Stripes
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The black blazer rocks silver glitter stripes down the sleeves that catch light when you move. A silver v-neck top peeks through, adding shine.
The wide-leg pants with matching glitter stripes stretch the legs for miles. This suit does that work, and that blazer structure means business.
Between the ring bling and that red lip, you’re giving CEO vibes. Perfect for dinner, dancing, or showing everyone at that party who runs things.
4. Power Red Long Sleeve Zipper Two Piece Set
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This wine red set brings drama to winter gatherings. Need an outfit that works from office to evening? This set delivers.
The fabric moves like liquid when you walk, and that color – it’s giving holiday party queen. Pair it with heels or sneakers, add some gold jewelry, and watch heads turn.
The high waist hits right where you want it, creating curves in all the right spots.
5. Khaki Knit Sweater Bodycon Two Piece Skirt Set
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This Khaki sweater bodycon puts in work for the cold months. See that pattern at the bottom? Those woven diamonds add movement when you walk.
The stretch knit fabric molds to your curves without squeezing. That matching tan purse and shoes pull it together – pure class.
The maxi length keeps you warm, and those geometric details at the hem? They turn heads at every holiday party or dinner date.
6. Abstract Art Multicolor V-Neck Rib Knit Sweater
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This sweater makes the rules. The pattern mixes oranges, greens, and pinks in swirls that catch light and turn heads.
That orange v-neck trim frames your face, while the relaxed fit hits right at the hip. Want to jazz up your basic jeans? This top does the heavy lifting.
The colors remind you of fall sunsets in Central Park. Perfect for brunch, gallery hopping, or turning that coffee run into your own street style moment.
7. Cozy Park Walk in a Cable Knit and Long Wool Coat
Start with an oversized cream cable knit sweater. It feels like a warm hug.
Pair it with black fleece-lined leggings—practical, right? Wear knee-high boots with good grip; NYC sidewalks in winter can be tricky.
Finish with a long wool coat. Imagine sipping hot cocoa in Central Park while the snow falls gently.
8. NYC Street Style in Faux Leather and a Puffer
Step into a sleek faux leather pencil skirt, paired with a turtleneck sweater.
Over that, throw on a shiny black puffer jacket, it’s so New York. Slip into ankle boots with thick soles; the streets are tough in winter.
Add a crossbody bag to keep your hands free for a coffee. You’re not just walking, you’re strutting down Fifth Avenue, owning the moment.
9. Baddie Casual with Distressed Jeans and Chunky Sneakers
Grab your favorite pair of high-waisted distressed jeans. Pair them with a cropped hoodie, it’s casual but cool.
Over it, layer a longline cardigan or a trench coat for warmth. Lace up some chunky sneakers; they’re practical for a day in SoHo.
You’ll feel relaxed but stylish, whether you’re window-shopping or hitting a food truck for a soft pretzel.
10. Broadway Night Out in Velvet Jumpsuit and Heels
Wear a black velvet jumpsuit. Its texture feels luxurious and festive.
Add tights for warmth, and slip on block-heeled booties for a little height without the pain. Drape yourself in a faux fur stole, it’s dramatic, just like Broadway.
You’re ready for dinner at a cozy spot before catching a show. Imagine the theater lights reflecting off your sparkly earrings.
11. Trench Coat Chic for a Snowy Day
Choose a tan trench coat, it’s timeless and keeps the wind out. Pair it with gray wide-leg trousers and a turtleneck sweater.
Slide into waterproof leather loafers; snow doesn’t scare you. Add a knit beret and gloves.
You’re channeling a Paris-meets-New York vibe as you navigate snowy sidewalks, maybe stopping by a bakery for something warm and flaky.
12. Night Out Glam in Sequins and a Leather Jacket
Wear a sequined bodycon dress; it’s the sparkle you need for a winter night.
Balance it with a cropped faux leather jacket to keep it edgy. Throw on tights and heeled booties that won’t slip on wet streets.
Carry a clutch with a chain strap, it’s practical but chic. Picture yourself walking into a rooftop bar, the city skyline glowing behind you.
13. Aesthetic Coffee Run in Neutrals and Knits
Go monochrome with taupe knit pants and a matching sweater. Optional, layer with a camel-colored wrap coat that flows as you move.
Step into white sneakers or slip-on boots for comfort. Carry a tote bag big enough for your planner and latte.
The minimalist vibe is perfect for mornings at your favorite Lower East Side café. You’ll feel cozy but put-together.
14. Snowy Day Errands in Layers and Lug Boots
Pull on fleece-lined black joggers for easy movement. Pair them with a hoodie and a padded vest, layers are key.
Add thermal socks and sturdy lug boots; they handle snow like pros. Wear a beanie and a scarf, both knit.
Whether you’re grabbing groceries or meeting a friend for soup, you’ll feel ready to face the cold without sacrificing style.
15. Weekend Brunch Vibes in a Sweater Dress and Boots
Slip into a knee-length sweater dress in a jewel tone. Over it, wear a belted wool coat, it shapes your silhouette.
Add tights and over-the-knee boots for warmth and flair. Grab a leather crossbody bag for your essentials.
As you head to a brunch spot in the West Village, you’ll feel effortlessly stylish and ready to dive into pancakes.
16. Soho Shopping Day in a Knit Midi Skirt and Chelsea Boots
Pull on a ribbed knit midi skirt. Pair it with a fitted turtleneck sweater tucked in. Layer with an oversized blazer for a polished but relaxed look.
Chelsea boots with chunky soles handle cobblestones like a pro. Add a small backpack for your shopping finds.
Picture strolling through Soho, pausing to check your reflection in boutique windows.
17. Central Park Black Denim Overalls and Puff-Sleeve Sweater
Try black denim overalls with a puff-sleeve sweater underneath. Layer a cropped, sherpa-lined jacket over it for warmth.
Choose waterproof ankle boots, perfect for snow-covered paths. Top it off with a knit beanie and matching gloves.
Walking through Central Park, you’ll feel the crunch of snow underfoot while sipping hot cider from a street vendor. It’s cozy and playful all at once.
18. Date Night Elegance in a Satin Maxi Skirt and Blazer
Wear a sleek satin maxi skirt with a fitted bodysuit. Add an oversized blazer for that effortless, layered vibe.
Block-heeled mules work for indoor and outdoor settings. Carry a small structured clutch for the essentials.
You’ll feel a mix of power and grace as you step into that dimly lit Tribeca restaurant. Candlelight will catch the subtle sheen of your skirt perfectly.
19. Brooklyn Bridge Walk in Wide-Leg Pants and a Shacket
Slip into wide-leg pants, they flow with every step. Pair them with a long-sleeve top and a flannel shacket for warmth.
Comfortable sneakers are non-negotiable for the long walk. A knit infinity scarf completes the look.
Walking across the Brooklyn Bridge, you’ll feel the chill but also the beauty of the skyline. The perfect balance for an iconic New York moment.
20. Museum Stroll in a Short Wrap Dress and Long Coat
Try a knit wrap dress, it flatters and feels comfortable. Layer with a calf-length belted coat to keep warm indoors and out.
Knee-high boots with a slight heel keep you stylish but steady. Add a crossbody bag to hold your essentials.
Wandering through the Met, you’ll blend in with the art around you. Plus, wrap dresses make transitions from room to room so easy.
21. Late-Night Lounge in Joggers and a Sherpa Hoodie
Throw on fleece-lined joggers for ultimate comfort. Pair them with a sherpa hoodie, it’s cozy and stylish enough for a lounge bar.
Finish with slip-on boots and a small crossbody bag. Imagine a rooftop lounge in Williamsburg, sipping a warm drink while the city lights glow.
You’re comfortable enough to stay all night but look ready for impromptu photos with friends.
22. Ice Skating Style in a Quilted Coat and Thermal Leggings
Wear thermal leggings for warmth and movement. Add a knit sweater and layer it with a quilted coat, it’s light but warm.
Waterproof boots with a grip make skating safer. Don’t forget a bold-colored scarf to pop in photos.
Gliding across the Rockefeller Center rink, you’ll feel a rush of cold air and excitement.
23. Chinatown Food Crawl in Cargo Pants and a Puffy Vest
Step into cargo pants, they hold everything from keys to snacks. Pair them with a long-sleeve top and a lightweight puffy vest.
Add slip-on sneakers for comfort and ease. A crossbody bag holds extras like a notebook or chopsticks.
Wandering through Chinatown’s bustling streets, you’ll grab dumplings, bao, and maybe bubble tea. You’ll feel practical yet trendy, ready for the tastes and sights.
24. Pier Sunset in a Knit hooded Jumpsuit and Coat
Slip into a knit jumpsuit, soft, stretchy, and easy. Layer with a coat that protects against the breeze.
Sneakers or ankle boots keep you grounded on uneven piers. Add a scarf that’s long enough to wrap twice.
Watching the sun dip below the horizon at the Hudson River Park, you’ll feel the city quiet down for a moment.
➜ Styling Tips for Plus Size New York Winter Outfits
1. Start with Base Layering: Your first layer makes or breaks your winter outfit. Think thin, stretchy pieces that hug your body without squeezing.
Cotton camisoles and long-sleeve thermal tops become your best friends. You want fabric that moves with you when you’re rushing to catch the subway or hailing a cab.
Pick pieces in black, white, or nude – these work under any outfit and won’t peek through your clothes.
2. Choose Your Power Piece: Every outfit needs that one piece that makes you feel like you own New York.
Maybe it’s a wrap coat that shows off your waist, or boots that make you walk taller. Find what makes you feel powerful and build around it.
When I’m wearing my camel coat with the perfect belt, I feel like I can handle any meeting or dinner date that comes my way.
3. Master the Art of Proportions: Balance is your secret weapon in winter dressing. If you’re wearing bulky boots, pair them with fitted pants.
When you pick an oversized sweater, match it with straight-leg jeans. This creates a shape that works with your curves, not against them.
Think about your body as a canvas – you’re creating lines that flow together.
4. Invest in Statement Outerwear: Your coat becomes your outfit most days in New York winter.
Pick one that makes you feel good. A wool coat that hits mid-thigh works for most body types. Look for details like a belt or princess seams that create shape.
Dark colors hide winter slush marks, but don’t be afraid of red or camel – they brighten gray days.
5. Pick Smart Accessories: Winter accessories do double duty – they keep you warm and pull your look together.
A wide scarf can hide a bulk of layers underneath. Leather gloves make you feel put together, even when you’re freezing. Choose pieces that work with multiple outfits.
Remember, you’ll be taking these on and off as you move between outdoors and heated spaces.
6. Focus on Footwear: Your feet carry you through New York – treat them right.
Find boots with grip soles for icy sidewalks. Block heels work better than stilettos on subway grates. Keep a pair of flats in your bag for office days.
Your boots should fit with room for thick socks, but not so loose they rub when you walk those city blocks.
7. Plan for Temperature Changes: New York buildings blast heat while streets freeze. Layer pieces you can remove without ruining your outfit.
A cardigan under your coat gives you options. Wear tights under pants on the coldest days – you can remove them at work.
Think about your whole day when you dress. Will you be outside? Inside? Both? Plan accordingly.
Final Thoughts
Let me tell you something…
Creating plus size New York winter outfits is about feeling confident as you walk those busy streets.
You know what? New York winters might be tough, but they’ve got nothing on your strength.
Whether you’re rushing to meetings in Manhattan or meeting friends in Brooklyn, you deserve to feel amazing in your winter wardrobe.
These are your toolkit for conquering the city, one stylish step at a time.
Remember, your size isn’t a limit – it’s part of what makes you uniquely beautiful in this city of millions.
I’m Theresa! A passionate writer and supporter of body positivity. Advocate of plus-size fashion. My mission is to curate the latest trends and timeless fashion for plus size women. I want to inspire confidence and creativity through fashion, helping curvy women express their unique personalities with every outfit.