I'm Breaking Up With My Beanie—The 6 Winter Hats I'm Embracing Instead

The monotony of winter outerwear can really do a number on the sartorial spirit during the coldest months of the year. I don’t want to credit it for my seasonal affective disorder, but I also won’t count it out. Instead, I’m switching it up this year. It’s hard to have many coats on rotation if you have limited storage, so hats are an easy and space-saving way to add a little more “oomph” to my winter styling.

Beanies have always been a zero-effort standby, and they also can look that way. I think it’s more than time to give them a break and step out of my comfort zone while still staying warm. With that in mind, here are a few winter hats I’ve tested out to keep in my cold-weather wardrobe cycle.

The Knit Bonnet

One of the more avant-garde shapes of my roundup, the knit bonnet is what I call the “balaclava lite”. An over-the-head hood with my face cut out is very warm, but feels too extreme for me in day-to-day wear (unless it's about 10 degrees or below)—a bonnet, however, is kind of a sweeter, easier-to-digest version. It definitely straddles the line of gnomecore (much like my venture into Birkenstock clogs), but it’s cozy and playful nonetheless.

I love this cheerful striped wool version from Damson Madder that I know will serve me well on super cold, grey days when my warmest coat (my long black Coach shearling) needs an optimistic boost.

The Leather Beret

I recently dug this one out from my personal collection—I received as a gift ages ago, and decided it was time to try to make it work.

Berets, though iconic, can just look annoying. I think the trick is wearing them a little more nonchalantly and a little less earnestly. The leather aspect of this one helps. I paired mine with a long leather Burberry trench I’ve had forever and some other feminine details, like a lace collar and pink sweater. However, I still felt a little too cutesy—I hate to say but, but almost a little too like Emily in Paris, which is an immediate buzzkill for me. (Even though I love the show!) I'll be experimenting, but I think a beret would seem even cooler with sportier jackets, like a puffer or windbreaker. Maybe something a little more casual, like a barn jacket or even a hoodie and sweats on a warmer day could work, too.

The (Faux) Fur Cloche

I recently complimented a girl on a warmer day this fall rock one of these with a lightweight leather jacket, and she looked cool and very '90s. (A tamer version of Pam Anderson’s pink one came to mind.) It was a risk that I knew needed some reinforcement, so I made it known to her and her date that I thought it looked great—so much so that I had to try it for myself!

The Apparis one I’m wearing here is technically a bucket, but the bushiness of the fur is so extreme, it reads more like a cloche shape when it’s on. I’ll be the first to say it’s definitely a little kooky and maybe too close to my hair color than I would have liked. But I enjoyed how '70s it looked with a retro texture, like a monochromatic corduroy puffer from Patagonia and my big everyday glasses. But if your personal style veers on the bold side, I say give it a go. On a sustainability note, if you’re looking for a non-poly version, brushed baby alpaca wool also has a similar effect.

The Shearling Bucket

A more paired-down version of the faux fur hat I tried is this faux shearling bucket from Ugg, which is a little less bulky and fits more like a traditional bucket hat. This one feels like a very easy grab-and-go option, which is ideal in my beanie replacement journey. I loved it with a striped shirt, knit vest, and funky Sacai jacket in the photo above, and I truly think it looks cute with just about everything. I would say maybe avoid pairing with other sherpa or furry coats, and use it only as an accent for texture against a wool coat, leather jacket, or puffer. Another sustainability note: Merino wool can also do a great job imitating real shearling and its poly dupe, if you have a personal conflict with either of those.

The Western Hat

Admittedly, wearing a western hat outside of Aspen in the winter definitely requires some grit. This is true especially for me in New England, but I enjoy the juxtaposition. With that said, I paired my wool cowboy hat that I seldom wear with a mens vintage patchwork Junya Watanabe puffer which felt so right. My head felt warm, and I liked that the brim gave me an air of mystery and also some protection from the wind, but it’s a lot of look. A western hat can definitely wear you in a sea of beanie-clad holiday crowds, so try pairing it with a very simple puffer or a long wool coat, and avoid anything super western, like a shearling or suede fringe.

The Ear Muff

For my final choice, I’d like to propose the ear muff. Full disclosure: I’ve never worn an ear muff. I don’t think it was something I’ve particularly avoided, but maybe I just got stuck in the beanie trap. For fear of feeling too prissy, I paired this white Coach one with some preppy touches, like a vintage Alpine sweater/college sweatshirt mashup from Rentrayage, a white collared shirt, and tweed jacket. There was a little hair finessing involved, but once I sorted it out, I enjoyed how incredibly cute they looked and how warm they were, even if they didn’t fully cover my head.

Something about an ear muff makes me want to go on an ice skating date. For that, lean right into a Hallmark holiday movie vibe and pair them with a feminine belted wool coat—and big knit mittens, naturally.