Living in NYC in the winter means you quickly learn that a good hat can make or break your day. Between the wind on the west side highway and the subway gusts when you’re coming out of the turnstile, some days you just need something that keeps you warm. In all of my years of having to look effortlessly chic, even in a snowstorm, I’ve learned that the right hat can completely elevate an outfit. Over the past season, I started noticing which hats kept popping up on stylish New Yorkers, from the women walking to work in SoHo to friends grabbing coffee in the West Village, and I took notes.
I’ve tested out a few for myself, and while some hats instantly felt classic and chic, others I quickly retired. After years of trial, error, and people watching, I’ve narrowed it down to six winter hats that actually get worn by NYC fashion people—and that I now reach for on repeat when the temperature drops.
Snood
From the ski lodge to the streets, the balaclava has officially entered the New York City group chats, and it couldn’t be cooler. It’s the perfect blend of chic and practical, keeping your face warm while instantly upgrading your winter outfits. So while it feels unconventional, it’s sure worth giving a try if you like being warm.
Newsboy Cap
I remember being in college when newsboy caps had their first takeover. Well, guess what? They’re back again. From corduroy to embroidered trims, NYC fashion people are loving how this cap elevates simple jeans-and-coat looks.
Classic Beanie
If you’re like me, you’re probably reading this and thinking, Well, yeah, beanies are everywhere in fall/winter. Sure, they're not groundbreaking, but it’s true. Don’t overlook this staple.
Baseball Hat
I know what you’re thinking. Baseball caps? But New Yorkers will do anything for fashion, so while it might not be as warm as other styles, it’s better than nothing and looks effortlessly cool. They’re ideal for running errands, grabbing coffee, or adding a casual edge to an otherwise tailored outfit.
Pillbox
Nothing says old-school glamour like a pillbox hat. It’s sleek, structured, and unmistakably chic, and instantly elevates your winter coat or wool dress. Fashion insiders in NYC have brought this throwback staple back into the limelight, and I’ve been loving it.
