Cool Winter Types of Hats You’ll Want to Wear Right Now

Think you can’t wear hats? Nonsense, you probably just haven’t found the right one. There is a hat out there for everyone, and this handy style guide can help you find your perfect match.

Having been a teenager in the 80s and early 90s, I spent a great deal of time protecting the integrity of my big hair. One of the hallmarks of the decade, my hair was in fact so big it actually extended beyond the frame of my driving license, giving the illusion of a floating, disembodied head in a deep sea of brunette, corkscrew-curled resplendence. Naturally, it was a perm.

Every year, my hair’s arch nemesis would arrive, usually about mid November, although sometimes as early as Halloween. The ground would freeze, plant growth would come to a screeching halt, and snow fell from the sky, forming into enormous heaps by winds so biting, they would make your nose hairs freeze together upon inhalation.

The weather conditions could become so vicious that the weather office regularly issued “flesh freezing advisories”, ordering us to stay inside our homes unless circumstances deemed it absolutely necessary to go out.

With all of this carry-on, you would think that we would have wanted to put on a hat to protect our heads from the cold. Did we? No, we did not.

We were so obsessed with our precious hair, we wouldn’t have dared wear something so potentially damaging (by which I mean flattening) as a hat. Instead, we chose the path of frostbite, broken-off bits of hair, and red, inflamed earlobes that could last weeks. It was torture, and winter in North America was a cruel, cruel mistress.

If only we’d known; it’s not only possible to keep warm and protect your hairstyle, but you can actually look pretty darn chic, or even have a bit of fun in the process. It’s all down to choosing the right types of hats for you.

Still have some residual doubt that you’ve been carrying around since 1987? Not to worry. This handy guide to winter hat styles should sort you out.

Best for not wrecking your hair – The Slouchy Beret

The Slouchy Beret

While there is certainly no way that you can wear a hat and not have some evidence of it left behind when you take it off, the oversized, slouchy beret is probably one of the most low-impact hat styles out there. Arguably, this type of knit hat was made popular in the late 90s, early 2000s by celebrity stylist Rachel Zoe, and can still be seen on her, as well as many of the starlets in her orbit.

For winter, an oversized, slouchy beret looks best in a chunky knit; something in a cabled or moss stitch works well. Despite their relative size, even a chunky- knit slouchy beret can be deceivingly lightweight, yet warm enough to allow you to stay comfortable as temperatures plummet.

Interested? Why not go right to the source and try one from Rachel Zoe’s eponymous clothing line. Like bling? She even makes a sequinned version.

Best for torturous sub-zero temperatures – The Trapper Hat

The Trapper Hat for Winter

Trapper hats have been on the scene for a while now, and while many versions that you see out there are purely fashion items, by design even the budget versions of this new winter staple are warmer than your average knitted wool hat. Most trapper hats are designed to be lined in fur (real or faux), or shearling, and are constructed using a heavier fabric like leather or canvas to provide warmth and support.

If you live in a place that gets properly cold (like, nose hair freezing cold), this is the hat for you. Despite it being quite a trendy design, your average trapper hat has functioning ear flaps, a forehead flap that folds up and down, and a string you can tie underneath your chin for when things get really ugly. But then, what are you even doing out there anyway?

Want to give it a try? Gant makes a flannel and faux fur version that is as warm as it is affordable.

Best for skiers and snowboarders – The Shaggy Stuffed Animal Hat

We may never understand the strange connection between skiing, snowboarding, and the affinity for wearing large, plush stuffed animals on top of one’s head, but the evidence is there. A bit of whimsy certainly never hurt anyone, and if there’s one thing that’s for certain, these faux fur shaggy creations are about as warm as it can get. If you want to go all-out, try an Eisbar hat; they are the official supplier of the Austrian National Ski Team.

Best to fit just about any head – The Simple Knit Beanie

The Simple Knit Beanie for Winter

For those of us who just want something they can reach for in a pinch and not have to worry about, the simple knit beanie should be the go to. Available in a multitude of sizes and equipped with a bit of stretch, these hats are as versatile as they are warm.

There are no limits to the possibilities of color and weave combinations, and if you need that little extra bit of warmth, you can fold the edge over to make a double layer to keep your ears warm. Worn unfolded, they take on a relaxed, 90s grunge appearance that looks just as chic with a t-shirt and jeans as it does with your winter woollies.

Still feeling unsure? Try treating yourself if this is your first hat experience – go for luxury! Knit hat designer Rosie Sugden makes her creations out of the finest Scottish Cashmere. Her creations are available in a variety of colors and patterns that look good enough to eat, and are as soft as…well, cashmere.

For most of us, the days of protecting our big 80s hair are long gone. In fact, hats have actually been making a bit of a comeback over the past few fashion cycles, which is good news for those of us who have to endure long, cold winters.

Despite what we believed back in the 80s, modern fashionistas (that’s you) are lucky in that they have more ways than ever to look chic, express themselves, and still be protected from the elements.

About the author

Kristin Buchholz-MacKillop

Kristin is an American writer based in the Scottish Highlands. She is a saxophonist, an obsessive tennis player, a U.S. Air Force Veteran, and holds a Master's degree as an Acute Care Nurse Practitioner. She is the author of the online style blog

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