New York in winter means sub-zero sidewalks, biting wind between skyscrapers, and a lot of walking — and yet the city's dressers refuse to disappear into shapeless black puffers. Stylists Maegan Watson and Sarah Slutsky Tooley have shared their playbook for winter 2026/27, and it boils down to one idea: make the warmth part of the look, not a cover-up for it.
Start with layers that actually hold heat. Watson favours cashmere, wool and shearling, citing knitwear from Prada, Khaite, Valentino and Guest in Residence. Her not-so-secret weapon is a tissue-weight cashmere turtleneck worn under a shirt, dress or jacket — it turns a non-winter piece into a winter-ready one. She also rates lace base layers from Ulla Johnson and Wolford, which add warmth while still reading as deliberate styling, ideally in more than one colour.
Skirts can stay in rotation too. Watson argues a wool skirt with wool tights and knee-high boots is often warmer than jeans — she swears by a padded nylon Simone Rocha skirt for days running around the city. And rather than defaulting to black opaque tights, she suggests experimenting with texture, pattern and colour. Extra insulation under a coat works the same way: a cashmere or faux-fur vest under leather, or a capelet over a jacket, beats throwing a down jacket over everything.
The coat itself is the main event in New York, where most of the day is spent outdoors. Watson predicts longer silhouettes for 2026/27 — trench-inspired wool coats with fur or embellished collars and statement cuffs — and loves a dramatic A-line swing coat in wool, suede or cashmere. Tooley takes a bolder route with an oversized white Acne parka cinched with a belt ('basically a sleeping bag', but polished, and apparently a smile-generator on the subway). If you're investing in one piece, Watson says this is where to spend: a single exceptional coat from a house like Valentino or Dior can reframe an entire winter wardrobe.
Then there's footwear. New York is a walking city, so boots need to go the distance on icy pavements without looking technical. Tooley has relied on Toteme for years for sleek, warm styles; Watson insists on a black leather boot with a comfortable block heel from Khaite or Prada, ideally with a rubber sole so a sudden cold snap doesn't catch you out.
For travellers, this is a genuinely useful packing brief. New York winter sightseeing means hours outside — walking the High Line, queueing for the ferry to Statue of Liberty — so the same logic applies: thin heat-retaining base layers, one statement coat you actually like being seen in, and waterproof-soled boots you can walk miles in. It's also a good excuse to shop while you're there; the city's department stores and boutiques are at their cosiest in January, when winter sales hit.
