Hats serve not only practical use for the winter season, but also a way to top off your personal style for any fit. Many of us are familiar with the classic baseball cap or beanie, easy to throw on over our months-long uncut quarantine hair. However, there are a bunch of other options out there that will help you accessorize and have a more modern put-together look.
The great thing about hats is that they’re super versatile, similar to the hoodie for clothing — men’s hats can be worn in a multitude of settings. During the winter months, we definitely look for hats that provide more warmth to our heads and ears. We recommend opting in for ones with a wool or fleece material as they tend to be the warmest.
Below we rounded up some of the best hats from our favorite online shops that aren’t only practical, but fashionable.
The Baseball Cap
Madewell Baseball Cap in Corduroy
If you’re like me you probably have so many baseball caps and don’t even know how, honestly. Well here’s another one that’s a must-have. Adding a modern twist to the classic baseball cap, this corduroy material adds a cool factor to the timeless style.
Kühl Überkühl Visor
It’s barely a hat. It’s pretty much all brim. It’s not gonna offer you a lot in the way of sun-protection. So why bother? ‘Cause it’s cool, both literally and figuratively. Suddenly we’re moving from just throwing something on our heads to making a statement. A visor shades the eyes just so, while allowing the top of the head to be free in the breeze. It functions as an ersatz headband. It offers a bit of mid-century modern style. This one from Kühl is made from a quick-drying cotton-blend fabric that is also extremely lightweight. We like it with tennis shorts, but it’s also a great complement to track suits.
A visor is a perfect option for outdoor sporting activities such as golf, tennis, or jogging. This sport performance visor will help protect your eyes from the sun (and your skin from damaging UV rays) while leaving your head cool and avoiding sweating hair, because who likes that?
The Bucket Hat
Levi’s Logo Bucket Hat
’90s fashion is back in full force! Including the bucket hat which can be seen all over the runway and your favorite celebrity these days. This bucket hat will keep you on-trend and functional at the same time.
BRIXTON Hooligan III Driving Cap
If you’re going for a more sophisticated look, a cap is one of your best bets. Perfect to be paired with a wool coat for the ultimate winter outerwear look.
Hampui Hats Atlantean Hills
It’s a misnomer. The classic Panama isn’t even from the South American isthmus. It’s actually from Ecuador. The classic white straw fedora was christened with the name when Teddy Roosevelt visited the construction of the Panama Canal and was photographed wearing the style. Since then it’s become a kind of standard for easy summer style with a bit of Hollywood flair. While classically rendered in white straw, we like this caramel-colored version from Hampui (be sure to check out their video about how Panamas are made) with its Shibori dyed band. It’s the perfect hat to keep on a hook next to the door. Throw it on for dinner out, a stop at the farmer’s market, or to mow the lawn with finesse. While it can finish a seersucker suit nicely, we like it tossed on with a simple t-shirt and chinos or shorts.
Dolce & Gabbana Panama style hat
This classic style has been making its way back into modern runways and fashion collections in the past two years. Perfect for the summer days this Panama style hat is peak luxury taste.
The Lifeguard Hat
Sunday Afternoons Sun Guardian Hat
We’re just gonna say it and then apologize. Yes. Skin cancer is a thing. It’s very bad. That is no excuse for bad style. Yes, there is some one percent of the male population that can make those floppy canvas wide-brimmed sun hats look good. They are all male models. The rest of us look like dweebs. There. We said it and we’re sorry. (But not really.) Yes. There are those days when you are nowhere near a beach umbrella or shelter of any kind. You should be protecting your noggin, your face, your neck, and as much of you as possible. The lifeguard hat offers the kind of coverage that, well, a lifeguard needs, without the nerdy affect. This one from Sunday Afternoons offers even more protection with a UPF 50+brim and liner, and an elasticized headband for an awesome fit.
Field & Stream Men’s Evershade Lifeguard Hat
This hat is more practical than fashionable, but still, I’m sure some of you can pull it off. Just as the name implies, this hat is a great go-to for someone whos out in the sun for long periods of time.
The Cowboy Hat
Stetson Open Road
Tread lightly here. There are places where only a true cowboy hat will work. Usually that’s where a true cowboy actually works. Maybe it’s a bar where a properly executed two-step is a rite of passage. The rest of us need a cowboy hat that can handle a family picnic or an outdoor concert. This hemp straw version from Stetson provides vintage-inspired style that feels classic and oddly modern. Pair it with a crisp white linen shirt or a serape-blanket inspired pullover.
Cavender’s Cowboy Collection 2X Black Wool Cowboy Hat
With celebrities like Lil Nas X bringing a fashion approach to the cowboy hat — the demand has been sky high among those who aren’t too advance on the range. This cowboy hat gives that urban touch while still holding true to the cowboy origins.
Brixton Messer Fedora
Here is where we cross the line. The fedora is your introduction to the world of grown-up hats. A felt version provides a little welcome extra warmth as we head into fall. Once the uniform of Everyman, it both requires and instills a level of confidence. It can dress-up a pair of jeans and a t-shirt and lend Silver Screen credibility to a suit. Take your time. Wear it around the house. Get used to it. Then wear it everywhere with everything.
Lack of Color Jethro II
A great option that can be worn year-round, the fedora is a timeless statement hat that is worn by people of many different style backgrounds.
Mack Weldon Tech Cashmere Hat
From beanies to watch caps and beyond, the knit cap is the winter version of the baseball cap. If you don’t have one we’re just assuming you have a really thick head of hair and don’t live north of the Mason-Dixon Line. From rappers to skaters to baristas, it’s become a uniform of sorts; sometimes worn ironically, perched atop the head, over the ears where it’s little more than ornament; sometimes pulled down tight for braving arctic tundra, ski slopes, and windy city streets. We like them best when kept simple. Eschew graphics and pom-poms for neutral or bright colors (have a few of each!). We’re particularly partial to this cashmere/merino blend that not only feels soft against the scalp, but also holds its shape and keeps your head warm. Wear it with an oversized t-shirt or a puffy jacket, but this one even looks great with a classic overcoat.
Desigual Tricot Cap Removable Letters
This fun knit cap is functional in more ways than one. This hat has removable letters to write out your own personalized message and super warm with a thick braided knit that covers the ears.
Read more: Best Beanies for Men
Nobis Nico Trapper Hat
In the 1950s hats with warming ear flaps were de rigeur for everyone from lumberjacks to rangers to sled-riding kids. By the end of the 20th century they’d been relegated to cartoonish characters embracing an Elmer Fudd sensibility. Today they are back, worn with more than just a little savoir faire; perhaps best worn when providing a kind of furry crown atop minimalist atonal silhouettes. We like this one from Nobis with a faux rascally rabbit lining. It’s a perfect way to round out your headwear wardrobe for winter’s coldest days while still maintaining your personal flair.
The North Face Canvas Trapper
I doubt many of us will be facing and super treacherous snowstorms … but who knows the way these past months have been going. Be prepared with this canvas trapper hat from North Face that will keep you warm and cozy in any frigid climate.
- Watch Cartoons Online: The Ultimate Streaming Guide
- The 9 Best Cycling Shorts for Maximum Comfort and Style
- The 21 Essentials You Need for a Trip to Yellowstone in 2021
- The 10 Best Loafers for Men to Buy in Spring 2021
- The 10 Best Camping Lights to Brighten Your Campsite