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Winter is coming and my ears are freezing off. So, I’m on the hunt for cute headwear. I’ve never thought that I look my best in hats. Maybe it’s insecurity or maybe it’s because it can be surprisingly hard to find the right hat for you. And to prove that, I came up with a list of deals and disasters for winter headwear. Let’s waste neither time nor body heat and get straight to the deals.

Felt hats always look fancy. They will dress up any outfit and look flattering on almost anyone. Felt material is normally made of wool so it will keep you warm, too. You just need to choose how broad you want the brim to be and what kind of crown (the top of the hat) and shape you want.

Nine West has a couple good options to consider: Wool Felt Telescope Floppy Hat and Felt Crown Panama Hat. Those hats will be like a cherry on top of your winter outfit and make it look like high street fashion. 

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MaxMara carries a wool felt hat with wide brims. It is decorated with a leather bond and adjustable ties. This is one of my favorites. It will look perfect with a camel coat, another staple of the season.

Then, I have two options that I would consider for a winter cabin or ski resort look (confession: I don’t ski) but I somehow can’t see myself wearing these in the city. They are: the Chapka Teddy hat and Busby Teddy hat by Max Mara.

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The chapka teddy hat will definitely keep your ears protected and warm with those floppy ear coverings. It’s made of 100% camel wool, too. Impressive, I know. It has a cool, versatile design as well. You can clip those floppy ears on top of the hat and create drastically different types of headwear. It reminds me of the USSR times though, which my relatives lived under. My grandparents used to keep such hats around and I always found them funny and somewhat rough. The Busby Teddy hat is described as having “a highly contemporary effect” but, again, it has older associations for me. While MaxMara made it from 44% virgin wool, 44% alpaca and 12% silk; my granny had a karakul hat of the same design.

For those of you who are wondering right now what a karakul hat is… it’s a hat made from sheep pelts with a curly pattern. This type of material is also known as karakul/caracul/Qaraqul, Astrakhan fur, or Persian lamb. I admit that these hats aren’t for everyone but paired in the right way, they could make you stand out, in a good way, and feel cozy.

Now onto the winter disasters… You know how bucket hats conquered the streets last season? Full disclosure: I had a light blue jean bucket hat when I was 7. Back then, I thought it was cool. Well, I grew up since then and so did my tastes. If summer bucket hats look so-so, in my opinion, the winter ones are flat-out ugly. Unless you want to pair it with an ugly Christmas sweater and be ironic or something… I found this bucket hat in faux suede and teddy on Asos. And while it costs only $20, think twice why they don’t even have a model wearing it, just pictures of the hat itself. Self-explanatory, isn’t it?

Asos designed a faux fur roll back bucket hat, too. In this case, they have a real face wearing this type of bucket hat but it didn’t help much because it actually looks like a witch hat for Halloween, which has already passed, so I don’t know why you would need this hat… 

But the worst is yet to come!

I was looking up hats for myself on the Macy’s website where they have a great variety of nice and affordable choices. When all of a sudden, I saw this conductor cap. Choo choo! It will make even a 16-year-old look old and shrivelled, out of place. But hey, it’s “distressed.” Now I do know why some people believe in time travel and claim that they saw people from an earlier age. If you’re attending a steampunk event, go for it! If not, buy one and put it on the nearest railroad tracks to destroy it. (I’m just kidding! Sustainability, people!) 

And the last “disaster” piece for this article is something I remember from my own childhood, this Scala Knit Wool Cloche with Flower. When I was 5 or 6, a relative of mine, who will remain nameless, bought something like this and even then I was like, BUT WHY?! This type of hat always makes you look older, not younger. You know you’ve missed the mark stylistically when a little girl’s intuition is like hey, um, no.

Unrelated:

I’m a fan of cowgirl hats, though you get a lot of looks if you wear them in cities where they’re not prevalent or really part of the culture there. Of course, they’re not appropriate for winter at all, but I think we’re all facing this winter with a bit of anxiety. So, here’s hoping we can hit “fast-forward” a bit and make our way to a normal spring and summer. Then, we can don our cowgirl hats triumphantly!