Men’s hats serve a key purpose in every well-dressed guy’s clothing arsenal. A great dad hat will shield your head from the sun’s rays. A trucker cap, or a baseball cap, or dare we say even a cowboy hat, will cover up any receding hairlines or poorly thought-out hairstyles. And it will add that final touch to a casual, or dressy, ensemble.
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Yes, some dudes are maligned for wearing hats. No, you won’t be one of them. That’s because we’ve hand-picked some seriously stylish chapeaus for all your needs, whether you’re wearing it to your kid’s Little League ballgame, or to a dinner out with your significant other.
Pros: Sure, you could throw in the freebie baseball cap you got from your local bar. Or you could step things up with this brilliant cap with a hidden interior pocket for stashing cash or a key. It’s a dad win. Plus the quality is out of this world.
Cons: For a baseball cap, it’s on the pricier end, for sure.
Pros: You’ll never want to take off this lightweight and breathable cadet hat, made from ripstop fabric for everyday wear and tear. The cadet hat has two inch brim and a three inch crown.
Cons: The hat can run small, so those with big head, order a size up.
Pros: While not exactly a snapback because you can adjust the sizing, this hat is otherwise a dream. You get a classic six-panel design with a curved bill and an adjustable leather back strap.
Cons: We love Filson, but it’s not for the budget-minded.
Waxed cotton has been a wet-weather repellent since the time of sailed ships. Stormy Kromer has been making hats from this classic fabric for more than a hundred years, and its idiosyncratic design is nothing if not effective when faced with moist conditions.
Pros: Made from a thick 10-ounce paraffin-treated cotton, the hat wears well over time, developing a patina similar to leather. Inside, a polyester and cotton lining keeps things cool and sweat moving. Finally, a pull-down earband, made from thick tweed, is a welcome addition during cold rains.
Cons: If you’re between sizes, go up.
Pros: Are you a stallion or a cock? Choose whatever animal represents you, or is close to your heart, and wear the hat with pride. It’s a trucker cap with an adjustable strap.
Cons: They tend to run small.
Pros: It’s the perfect cap to slip on when you’re doing the school or coffee run. You get a classic trucker design, with an adjustable snapback closure at the rear. The circumference is 18 inches, with a brim that 2 3⁄4 inches.
Cons: Again, this is a personal style issue. If you’re not into trucker caps, opt out.
Pros: A timeless, classic Panama hat straw design that you can wear to the beach, the boat, or a wedding.
Cons: It’s a bit, well, much. For some at least.
Pros: With C. C. Filson, you’re getting a hat with serious heritage, dating back to the 1890s. This style in particular is made of leather, and lined with a cotton sweatband. It has a 24 inch brim. And you can spot-clean it.
Cons: It’s leather, which may not be your thing.
Pros: Made from Stetson’s legendary fur felt blend, this hat cinches down on your head thanks to a leather sweatband that breaks in over time. The brim, while offering protection from the noonday sun, isn’t so wide and the crown so deep as to feel at home on the set of a Spaghetti Western. The heritage brand draws from generations of hatmakers to channel American iconography.
Cons: With a pricetag to match its years, this isn’t a cheap option. But Stetson’s quality is why it’s remained in business for more than 150 years. If you get what you pay for, you’re getting a lot with the Open Road.
Pros: Made from a sun-blocking UPF-50 synthetic material, the Bora Bora II also has a moisture-wicking sweatband to keep you cool. We love the modern addition of a mesh panel for increased airflow. Just like its predecessors, this has the trademark drawcord to keep the cap in place during windy days or high speeds on the water.
Cons: While its drawcord keeps the hat in place, its fit is largely guaranteed by an elastic sweatband, which only comes in two sizes. Make sure you measure your head to end up with the best fit.
Pros: Made from woven straw, this is a design based on many you’ll find around the world’s tropical islands and beaches. An elastic band keeps it tight to the noggin, while the small spaces through the weave ensure that air passes with ease. A drawcord ensures it stays close.
Cons: Natural fibers always wear out before synthetics, and this hat offers the most extreme example. While the straw can take some hits, it’s still a dry, brittle material, and as such, it will break down under hard wear.
Pros: With its two and a half inch brim, plus UPF 50 sun protection, you’re keeping the rays at bay with this Panama Jack hat. Made out of a canvas cloth material, this sun hat has an inner sweatband, to keep things cool.
Cons: Practical? Hell yes. Trendy? Not so much.
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