The Coolest Winter Hats Will Keep You Warm All Season Long

For the longest time, winter hats—nay, hats en masse—didn’t really register with me. Man, if you saw the beautiful head of hair, which I meticulously coiffed every morning before school, you’d understand why. I liked showing off my best assets (still do, in fact) and covering them up didn’t make sense. Even during the bitterest of winters, when snowfall was near constant for months on end, all I would do is shroud my head with a hoodie, never tightening the drawstrings so as to keep my gelled side-part intact. Needless to say, I argued with my mother often. I also got sick often. My petulance always got the best of me.

Admittedly, I did gravitate toward berets for a hot minute, only because I started becoming a Francophile, which coincided with my discovery of Mary Tyler Moore. That phase didn’t last too long. Then, around the late ’90s, I became fascinated with newsboy caps, largely because of LL Cool J, who began wearing the style, almost exclusively by Kangol, post his bucket hat period and his pre his station in the land beanies. That was also a fleeting period.

Now, come winter, I wouldn’t be caught dead without my head encased tightly and securely in wool, cashmere, or something lined with fleece. Wisdom comes with age, and from experience, I’ll do anything to not be sick in bed, surrounded by bottles of DayQuil and NyQuil, cups of throat-soothing tea, and mounds of used Kleenex. If I do have to step out in the cold, I’ll take my pick from my closet of hats—from buckets and beanies to caps and berets—that are all made of insulating fabrics and materials. It’s about performance first and foremost, but that doesn’t mean I forgo style completely. And if you, too, learned the hard way about why wearing a hat in winter is a necessity (or maybe you just listened to your parents from the start), check out the 17 below that’ll keep you comfy, cozy, and, hopefully, sniffle-free.