As the mercury dips and the world transforms into either a wet and windy soup of leaves and rain, or more preferably, a snowy wonderland, there’s one crucial element that often stands between you and the biting chill of winter: headwear. In the frosty months, what you choose to crown your bonce with can make all the difference between shivering discomfort and cozy warmth.
From classic beanies to heritage inspired trapper hats designed for colder climes, we’ll make a collective case for the headwear we reckon deserves a place of prominence in your winter wardrobe.
Arc’teryx Bird Word Toque Beanie
Recent winters have seen that bird soar higher and higher. As Gorp goes mainstream, this is the sort of brand you’ll see more of, but it’s popular for a reason.
Get it here
Noah Heart Mountain Beanie
We all love love don’t we? And we all love Noah, too. So Noah doing something with love hearts on it? Love.
Get yours here
Arc’teryx Bird Head Beanie
Another inclusion of Arc’teryx so soon into the list? You betcha.
Get it here
66° North Dyngja Knitted Beanie
Icelanders know a thing or two about harsh weather. Trust them by wearing this Dyngja beanie from 66° North.
Get it here
Service Works Logo Watch Cap
A brand that somehow takes sartorial inspiration from chefs is surely worthy of additional consideration. This beanie from Service Works has some smart, standout branding.
Get it here
Pleasures Everyday Beanie
This is the only sky blue hat in this collection, because it’s a colour hard to pull off, unless you’re a regular at the stadium in East Manchester.
Get it here
C.P. Company Merino Wool Goggle Hat
No beanie list would be complete without the inclusion of this strange yet popular creation from C.P. Company.
Get it here
RRL by Ralph Lauren Plaid Wool Earflap Cap
Make like a cool Elmer Fudd. You know who Elmer Fudd is don’t you?
Get it here
Wild Things Polartec Flight Cap
A tech take on a traditional trapper. Try saying that after a trio of tinctures.
Get it here
Mountain Equipment Citadel Hat
A personal favourite within this entire list. Mountain Equipment have never really sought style conscious tribes but in shunning fashion they’ve endeared themselves to that crowd.
Get it here
Klattermusen Draupa Hat
Super Swedes and their brand named after a climbing mouse, Klattermusen are always welcome on this website.
Get one here
Hikerdelic Trapper Cap Black
Oh look it’s one of ours.
Get it here
Pop Trading Company x Paul Smith Embroidered Corduroy Cap
Benetton vibes from this meeting of minds between Paul Smith and Pop Trading.
Get yours here
Patagonia Range Earflap Hat
This feels distinctly un-Patagonia, but why not give it a chance? We would.
Get it here
Fjallraven Singi Field Cap
Another contender for the crown (lol) of best hat on this list. There’s something about that short peak isn’t there?
Get it here
Meanswhile Uneven Fabric Cover Cap
A jumbo cord version of something Sherlock Holmes would have donned while solving crimes.
Get yourself one here
Carhartt WIP Prentis Bucket Hat
Can’t decide if this puts us in mind of Legally Blonde or Jamiroquai. Either is fine.
Get it here
Columbia Winter Pass Reversible Bucket Hat
Two hats in one, should you wish to procure something with genuine value.
Get it here
Gramicci Shell Bucket Hat
This pattern pervades Gramicci’s range this season and it looks like a psychedelic swimming pool. Good, isn’t it?
Get it here
The North Face Class V Reversible Bucket Hat
Halfway between Japan-chic and Nanna-chic.
Get one here
Fjallraven x Specialized Hat
Really nice shape, nice branding and generally a lovely piece of hadwear.
Get one here
Palace Skateboards T&D Ripstop Boonie Hat
Always room for something completely off the wall, which is what you want from Palace isn’t it?
Get it here
Beams Plus Jungle Hat
Taking design cues from jungle military wear, this is almost not really a bucket hat.
Get it here
Kavu Organic Strap Bucket Hat
Like the one above, this adjustable beauty has a mad wide brim for those of us who want to case additional shade over our face.
Get one here
And Wander 60/40 Cloth Hat
Are we still talking about Gorpcore? Because if we are, this is that, to a tee.
Get it here
Cotopaxi Tech Bucket Hat
Suitably summer vibes in this hat, if you’re in a part of the world where it’s summer, that is. Not everyone who reads this is looking to embrace the Northern Hemisphere’s wintry selections. Off somewhere nice? Get this.
Get it here
Pop Trading Company Pop Bell Hat Brown Gingham
LL Cool J’s uncle wears this to do his shopping in, and frankly, you can’t get cooler than that. (He doesn’t, but you could imagine it, couldn’t you?)
Get yours here
Goldwin Compact Jet Cap
Caps are a year round item, and while they’ll keep the sun off your face in summer, their winter function is just as key. This is defo in that camp.
Get it here
Lacoste Core Logo Baseball Cap
The best logo in fashion, we reckon. Something about that croc and its connotations add an air of desirability to what is otherwise a pretty regular cap.
Get it here
Columbia ROC II Ball Cap
Another vote for Columbia, with this run of the mill, reliable headwear.
Get it here
Snow Peak Light Mountain Cap
Another example of a piece of headwear with a slightly altered shape, that is all the better for it, this Snow Peak beauty will serve you well whenever you wear it.
Get yours here
Barbour Galingale Tartan Hat
The checked cap can conjure up casual connotations, but in this Barbour effort, something a bit different is brought to the table.
Get yourself one here
Gramicci Lightweight Shell Cap
Another entry into the list from the ever-reliable Gramicci, this shape of cap is synonymous with the outdoors.
Get yours here
Noah Core Logo Hemingway Cap
We’ve always loved Noah here at Proper, never more so than when they take an ostensibly casual item and make it somehow luxurious, via waxed fabric and leather fastening. Luxury Scruff.
Get it here
Noah Fisherman Knit Beanie
We’re onto bobble hats now and have remained with Noah. They’ve always done hats really well.
Get yours here
Carne Bolente Robite Hood
Though this calls itself a hood it’s basically a balaclava. Remember in the 80s when we were sent to school with mittens on a string to ensure we didn’t lose one? Halcyon days.
Get it here
Wild Things Polartec Neck Hoodie
Another balaclava that is claiming to be a hood, with some justification, it has to be said. This polartec layer is ideal to throw on when it’s really, really cold.
Get it here
