Though below-freezing temperatures can make it tempting to hibernate indoors, New York in winter doesn’t mean dressing for the cold at the expense of style.
Quite the opposite: the season brings out some of the city’s most considered looks, from dramatic coats and clever layering to designer boots made for icy sidewalks. The trick is balancing warmth with everything else you want to wear.
“At the end of the day, you do have to be practical,” says stylist Maegan Watson. “But practicality doesn’t have to mean sacrificing style.” That balance, she admits, is easier said than done. “The hardest part is finding pieces that are warm, stylish, and versatile at the same time,” Watson says. “That’s part of why stylists have jobs.”
Dressing for extreme cold doesn’t have to mean covering your outfit with an indistinct layer. “You absolutely can be exceptionally warm without automatically reaching for a black down coat,” Watson says. “You just need pieces made from materials that are actually designed to retain heat, and you need to know how to layer them.”
So, what actually works when the temperature drops? From the layers worth building a wardrobe around to the coats and boots that can handle a New York winter, here’s what the experts recommend for New York winter 2026.
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Layering is key
In terms of where to start, Watson reaches for cashmere, wool, and shearling, each of which provides a natural warmth. “Prada knits are a favorite, and I also love Khaite, Valentino, and Guest in Residence for beautiful cashmere and knitwear,” she adds. Thin layers can make a particularly big difference. Opt for a tissue-weight cashmere turtleneck, which can be worn underneath almost anything, from a cotton button-down to a dress or jacket. “Suddenly you’ve taken something that wasn’t necessarily a winter piece and made it work for winter.” Watson also recommends adding a lace base layer, her favorites available from Ulla Johnson or Wolford. “It can go underneath a jacket, dress, or button-down and adds warmth while still feeling intentional and styled,” she says, adding, “I love having them in multiple colors.” And, with the right layering and material, there’s no need to pack away your skirts, even in the depths of winter. “People can also be afraid of skirts when it’s freezing, but sometimes you’ll actually be warmer in wool tights, a great wool skirt, and knee-high boots than you would be in denim,” she says. “I have this amazing filled nylon Simone Rocha skirt that’s incredibly warm and cozy. When I’m running around New York seeing clients in the winter, that’s the skirt I reach for.” Tights offer another opportunity to bring some personality to a winter outfit: rather than defaulting to black opaque styles, Watson suggests playing with texture, pattern, and color. The layering principle applies to outerwear, too. A cashmere or faux-fur vest under a leather coat, or a leather, shearling, or wool capelet over a jacket, can add warmth, “without defaulting to putting a down jacket over every outfit.”
Make the coat the outfit
In New York, the coat is not simply something to throw on before heading out. “Your coat is such a major part of your wardrobe in [here] because so much of your day is spent moving through the city in it,” Watson says. “It shouldn’t feel like something you’re simply putting over your outfit. It can be one of the most important parts of the outfit.” For winter 2026/27, Watson is seeing longer silhouettes, particularly long, trench-inspired wool coats with details such as embellished collars, fur, or faux-fur collars and statement cuffs. “There’s something very luxurious about outerwear having movement and personality again,” she says. Her favorite stule? An A-line swing coat, in wool, suede, and cashmere. “For a coat to have that beautiful circular, A-line movement, it requires quite a bit of fabric, which gives it this wonderful drama.” Sarah Slutsky Tooley, celebrity stylist and creative director, takes a similarly statement-making approach. Her winter favorite is an oversized white Acne parka – “basically a sleeping bag,” – but a belt at the waist keeps it feeling polished. “It’s so massive and warm but has a belt to cinch the waist so I still feel chic,” she says, adding, “It always elicits loads of smiles when I wear it, I think New Yorkers love to see something different.” For Watson, a coat is also one place where it can make sense to invest. “If you want to make a true fashion investment, buy from a house like Valentino or Dior,” she says. “One exceptional coat can completely change your winter wardrobe.”
Add a pair of boots
New York is a walking city, so winter footwear needs to cope with the weather as well as the miles. According to Tooley and Watson, the key is a trusty pair of boots that can handle both. Tooley’s go-to is Toteme: “All my favorite winter boots are from Toteme – they are sleek, warm and have been my go to for years.” For Watson, it’s about finding a boot that can handle New York’s changeable weather without looking overly technical. “A black leather boot with a block heel that’s actually comfortable for walking is essential,” she says, pointing to styles by Khaite and Prada. A rubber sole, she says, is always useful: “you’re prepared if the weather turns without sacrificing style.” Ultimately, stylish winter dressing is about embracing, rather than fighting, the cold. “For me, staying polished in winter isn’t about covering a beautiful outfit with something warm,” says Watson, “It’s about making the warmth part of the styling.”
