Headwear during the cold winter months is absolutely essential, and with the cold weather well and truly here a winter hat roundup is long overdue. With the increasing variety of headwear among menswear fans we decided that it wasn’t enough to just highlight everyone’s winter staple, the beanie. 2021 saw a massive influx of people wearing masks of all kinds, and balaclavas have been a major part of that. Additionally, this winter has been the season of the detached hood, an item which we have been very enthusiastic about in the harsh winter months. The best trend of this winter, however, has to be the bold hat choices seen on celebrities such as A$AP Nast and Lil Yachty, who are often seen sporting large colorful hats. To accommodate for all this interesting stuff, we’ve broken up our list accordingly with some of the best winter hats for men to cozy up in the season ahead. Enjoy!
The Best Beanies
- Best Overall Design – Arc’teryx Bird Head Toque
- The Most Convenient – Champion Logo Cuff Beanie
- Best Luxury Beanie – Stüssy Helvetica Jacquard Beanie
- Warmest Beanie – Rag & Bone Wool Beanie
- Most Innovative Beanie – C.P. Company U16 Extra Fine Merino Wool Goggle Beanie
- Most Colorful Beanie – Aimé Leon Dore / Drake’s Ribbed Donegal Beanie
- Most Versatile Beanie – Eckhaus Latta Terrain Hat
- Boldest Beanie – Mowalola Blue Munchies Beanie
- Best Striped Option – Loewe Stripe Hat
- Most Affordable – Carhartt Knit Cuffed Beanie
- The Most Reliable – Polo Ralph Lauren Men’s Cuff Beanie
The Best Bavaclavas and Detachable Hoods
- Best for Anonymity – Arc’teryx Assault Balaclava
- Most Accessible Balaclava – Carhartt Fleece Balaclava
- Easiest To Work With – COS Hooded Mock Collar
- Best Knit Balaclava – 3.1 Phillip Lim Chunky Knit Balaclava
- Most Unique Balaclava – Greater Goods Hand-Knitted Balaclava
- Silliest Balaclava – Andersson Bell Purple Sullivan Balaclava
- Best Dual-Purpose Balaclava – Burton Polartec® Brimmed Balaclava
The Best Fuzzy and Furry Hats
- Warmest Hat – Eddie Bauer Truckee Faux Fur Trapper Hat
- Most Comfy – Salomon Sweet Life
- Most Stylish Fuzzy Hat – L.L. Bean Mad Bomber Hat
- Most Creative Fuzzy Hat – Story Mfg. Crocheted Organic Cotton Bucket Hat
- Best Designed Fuzzy Cap – R13 Faux Fur Bucket Hat
- Best Quality Fuzzy Cap – J.W. Anderson Asymmetric Bucket Hat
- The Holy Grail of Fuzzy Hats – Marni Textured Ear-flap Hat
- Most Stylish Option – Canada Goose Aviator Hat
Beanies are the all-time classic winter hat. They do exactly what you need them to, and nestle your head in their tight embrace. Most importantly, they keep your ears nice and toasty on those harsh windy winter days.
Buy in to a little bit of Arc’teryx logomania with one of their classic bird head toques. These are ideal for layering under hoods or helmets if you’re skiing, as their low profile keeps close to your skull. These are high quality warmth at a reasonable price. Also, if you can find one of their grotto toques pick one up, but they are almost always sold out.
Note: You may have to go in-person to an Arc’teryx store to cop one of these, or keep your eyes on the link below and wait for a restock.
At some point in the next couple of months, a good percentage of you will probably be getting an Amazon gift card for the holidays, so let’s help you out here. There’s a number of winter hats/beanies that you can grab on Amazon. Our favorite is the slouchy beanie, which has a pretty cool look.
Stüssy has returned to the streetwear scene with a vengeance, seemingly surpassing Supreme as the premier brand within the space. They have been pumping out tons of awesome hat designs, with this simple logo beanie being a personal favorite of ours.
Available in three colors and made with wool to keep you warm and cozy, the Rag & Bone Wool Beanie is an excellent choice this winter season. Practical yet fashionable.
C.P. Company has definitely been having a moment lately, with their goggle jackets and hats taking the spotlight. Here we see the classic goggle look has been applied to a beanie, keeping your head warm and your eyes fresh.
Aimé Leon Dore has been on a tear with the high quality basics, and this waffle knit option provides some great texture to a minimal style. There are a lot of fun color options, get them while they’re in stock.
Eckhaus Latta might be more commonly known for their eclectic womanswear, but this knit beanie transcends gender norms. The luscious knit and subtle coloring makes it a perfect addition to any winter wardrobe.
If these are looking a little quiet for you, grab this beanie from Mowalola that features her now-iconic flipped Walkman logo. This would go great with a louder wardrobe that echoes the recent neon craze.
J.W. Anderson’s Loewe just screams charming luxury, and the fun coloring and striping of this beanie can add some flair to your otherwise bland winter outfits.
You can’t beat the $20 price and quality. Plus, it’s Carhartt.
And when in doubt, go with Ralph Lauren. They are one of the longest standing brands out there, and offer a wide selection of winter hats.
Balaclavas and detached hoods are at the forefront of winter fashion right now, and we are loving it. One step up from a beanie, these can keep your head and neck warm all at the same time, while having the ability to be worn in a number of different ways. Leave your face covered or uncovered, or pull the hood all the way down to reveal your matted hair while keeping your neck pleasantly snug.
Feeling shiesty? We got you. Arc’teryx not only perfected the basic beanie, but they also have the black balaclava on lock. There’s nothing extraneous here, and it does exactly what you need it to.
This awesome balaclava from Carhartt is made of a super soft fleece, and the cord toggle lets you decide how tight you want the hood to sit around your face.
We’re not quite sure where this piece fits in within the balaclava and hood realm, but its way too cool to pass up. It features a large padded hood with a zip-up mock collar to make for an accessory that we promise nobody else has right now.
This phenomenal knit hood from Phillip Lim is huge, ensuring that there is absolutely no chance you get cold this winter. Coming in a beautiful mix of brown and white, the knit pattern feels beautifully crafted and homemade. It even features a sort of bib that goes down over your chest and back.
Unfortunately, these balaclavas can be a little tough to get your hands on, as they are each hand made and thus limited in their release. However, they are simply so beautiful that we need to keep them in this list. Each balaclava is completely unique, so you know you’re getting a special and personal item. If you really want one now, they do pop up on the secondhand market from time to time.
This entry from Andersson Bell, as is the case with all of the designer’s eclectic work, is a bit of an accent piece and a deviation from many of the more minimal options on this list. This is one of the best winter hats for men in your life who like something a little daring.
This entry from Burton is a great option for performance, as the brim will keep snow and other falling debris from getting in your vision.
Fuzzy and furry goodness has been all the rage this season and we are so here for it. Not only does it offer warmth, but the textural contrast added to any outfit is awesome, and makes for a bit of lighthearted fun.
Channel your inner 1800’s French Canadian with this faux fur hat from Eddie Bauer. It has some loose ties at the bottom so you can fasten the ear flaps to each other and stay as warm as possible.
This Salomon cap subverts the classic 5-panel by adding some fleece on the outside. The Sweet Fleece is a nice and cozy alternative to a traditional baseball cap.
L.L. Bean continues to be an all-American classic and their offering to the fuzzy hat game is as all-American as it gets. The classic bomber hat style has been around forever, and has become the quintessential fuzzy winter hat.
This bucket hat from Story Mfg. is one of the most versatile and unique pieces of headwear available right now. Kyrie Irving has been wearing one recently, and the hat is versatile and lightweight enough to wear year-round.
The chunky furry bucket hat craze is certainly here to stay, and this entry from R13 is a super fun one to have you feeling like Jamiroquai in the mid-90s.
J.W. Anderson’s namesake brand has been pumping out quality designs just as much as Loewe, and this hat is a testament to the designers panache. The shearling texture keeps this bucket hat a little left field, while the colors make it ideal for matching a winter wardrobe.
This Marni hat is an absolute grail and can be worn in a multitude of ways, with the flaps down or folded up alongside your head. The beautiful hit of pink along the top makes it sure to catch everyone’s eye as you walk by. The price point is certainly insane.
Available for both men and women, the Canada Goose Aviator hat lives up to its name with buckle down insulation and an adjustable chin strap. The hat is also water-resistant and well-built enough to keep you warm all winter long.