Best Men’s Hats for Every Occasion in 2021

Keep your head warm this winter with a classic Carhartt Acrylic Men’s Hat. This versatile design is simple to wear and easy to put on. It has become a favorite of the working man and city slicker alike, since it pairs well with a variety of styles, and, well, just plain keeps you warm.

These popular men’s hats come in a range of different colors and designs so you can choose one to blend with your outfit or choose something bright and outlandish as a stylistic focal point. They are made of a warm 100% acrylic stretchable rib-knit fabric that features the Carhartt label on the front. Match it with any of these stylish and warm scarves from our list for a perfect winter outfit.

This Belfry Gangster 100% Wool Stain Men’s Hat can add a charming and distinguished finish to your formal outfit. These 1920s men’s hats have a daring gangster appeal that will give you an air of mystery when you wear them with the right suit and some nice gloves—and who are we kidding, who doesn’t want to look like Shia LaBeouf in the movie Lawless?

These hats are made with a 100% soft wool body with a grosgrain sweatband that wicks moisture away from your head so you can stay cool, even with your hat on. They also have excellent water and stain resistance, and are designed for easy packaging. It is somewhat crushable but will bounce back into shape once you take it out of storage. Ideal for formal and not so formal occasion, this is the type of hat that is stylish and functional for the man who wants something iconic perched on top of his head.

Step out in this Wonderful Fashion Herringbone Tweed Wool Blend Men’s Hat and keep your head warm this winter. This newsboy style hat has been popular for a century and is still a stylish hat to wear, especially in winter. The outside features an easy-to-clean tweed wool blend, while the inside sports a quilted lining that gives your head a little extra insulation.

The classic design of these trendy men’s hats makes them suitable for most men to wear with their entire wardrobe. You can wear them with almost anything from classic or distressed jeans and a nice wool coat to a casual suit. This hat is available in a range of patterns and colors to match them with your wardrobe’s color palette.

Some types of men’s hats simply stand out more than others, like this Brixton Medium Brim Felt Men’s Hat. This is a true gentleman’s hat with a 100% will-knit weave in a range of colors that belie elegance without screaming about it. This flat-brimmed fedora features a versatile and timeless style that is suitable for young or old alike. It has the perfect fit and feel, so you can step out with complete confidence and keep your head warm too. Pair it with a trench coat for a truly timeless look.

Some of the coolest men’s hats are the simple ones, like this Under Armour Blitzing Men’s Hat. This baseball-style cap is perfect for a day in the sun along with a nice V-neck t-shirt. The pre-curved visor and structured front panels give this cap a nice shape and add a little foam padding for a touch of comfort. It features the UA classic appearance and stretch-construction for a comfortable fit. This hat is easy to throw on with any outfit, and looks good, no matter how you flaunt it.

The Quicksilver Men’s Pierside Straw Hat is a 100% raffia straw hat that is perfect for a day at the beach, a picnic in your favorite park, or even when you need a deep-sea fishing hat. These wide-brimmed men’s hats from Quicksilver have an adjustable closure as well as an adjustable chin strap to keep your hat securely on your head, even on a windy day.

These cool hats feature the Quicksilver logo patch and can be worn on a casual outfit or even just relaxing under a beach umbrella. Plus, they’ll keep your face from harsh sun rays, so you’ll always look your best.

The Home Prefer Thick Knit Beanie Men’s Hat is one of those unique men’s hats that offers you the combination of a super warm winter beanie alongside the sun-protecting visor of a panel hat.

This hat is made from a combination of acrylic and wool with a 100% polyester lining to keep your head toasty warm. It is soft, warm, and comfortable enough for even the chilliest day. Best of all, the visor makes it ideal for cold days when the sun is shining brightly. This is perfect for winter sports enthusiasts and those who won’t let a bit of cold keep them locked indoors.

The rugged outdoorsman will love the Quiksilver Men’s Bushmaster Floppy Bucket Hat. These are some of the best hats for men who consider themselves to be weekend warriors. These bucket-style hats are made from 100% cotton twill fabric with a pull-on closure and adjustable chin strap. This wide-brimmed men’s bucket hat is ideal for a day in the sun whether you’re playing golf, going for a hike, or even engaging in a paintball squirmish with your buddies. They are available in a range of colors so you decide whether you want to blend into your surroundings or stand out.

Early morning commutes or evening strolls with your date can leave your noggin feeling the sting of winter’s chill. This Amazon Essentials Men’s Trapper Hat with Faux Fur is a classic hunter’s style of hat, so even during the coldest activities, you can stay warm. These trapper hats are made with a blended shell of acrylic and polyester with a 100% polyester lining for added warmth. This hat should be at the top of your extreme cold weather gear list.

This groovy hat has a snap closure with an adjuster that secures the hat to your head. This thick, insulated style preserves heat so your head stays warm even in the chilliest weather.

If the Aussies know anything, it’s how to stay cool on a hot day. The Henschel Hats Aussie Breezer Men’s Hat is perfect for those sunny days when you want to feel and look cool. This hat is made from cotton with a mesh shell that helps keep your noggin cool. The brim is wide enough to protect your face from the sun and the self-adjustable chin cord means you can secure your hat, even on a windy day.

This hat is stylish enough for a round of golf or a country club barbecue, but also casual enough for a pool party or a day in the beach chair.

This Jeff & Aimy Unisex Winter Elmer Fudd Earflap Hat is a combination of style, fun, and function. The unisex military trapper style hat features faux fur ear warmers with a quilted lining. It also features a snap-locked chin strap to secure the hat to your head and keep your ears warm.

To protect you from the elements, this hat also uses a baseball-style vizor to keep sun, rain, or snow from getting into your eyes. The elastic cord ensures you have a great fitting hat.

Stylish men’s hats don’t get much better than this Jeff & Aimy Men’s Wool Blend Knit Newsboy Cap. This hat is the perfect combination of warmth and fashion. The hat is made from an insulating wool blend to keep the heat around your head, while the moisture-wicking sweatband prevents you from overheating.

The protective brim of this hat keeps the sun and other elements away from your eyes, making this hat perfect for special daytime events as well as romantic evenings outdoors in the snow. If you are into modern headwear, make sure to also check out our selection of the best Bluetooth beanie hats for men.