Best Men’s Hats for Every Occasion in 2021
Everyone should have at least one good hat in their wardrobe. The trouble is, how do you find the right one for every occasion? There is no one end-all-be-all hat for every occasion, as there are too many different types of men’s hats for different activities. Not all that long ago, hats were a must-have accessory in any gentleman’s wardrobe, but ever since the end of WWII, the popularity of hats has steadily declined.
So why should we still be wearing hats? For starters, hats have a purpose. They can either be worn to keep your head warm during winter or to keep the sun out of your eyes in the summer. Hats can also be super stylish and worn to formal occasions. If you think you’re too hip to be wearing hats like your granddad used to, think again. Hats have never really gone out of style! We’ve gathered some of the best men’s hats for every occasion so you can revive this artful accessory.
The Best Men’s Hat
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.
100% acrylic stretchable rib-knit fabric
Hand wash only
Carhartt label sewn on front
Extensive range of colors
- Weight2.4 ounces
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.
100% soft wool body
Excellent water & stain resistance
Crushable, packable design
Ideal for formal occasions
- Weight5.29 ounces
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.
Herringbone winter hat for men
Suitable for most people
- BrandWonderful Fashion
- Weight3.21 ounces
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.
100% wool knit weave
Hand wash only
Flat brim fedora
Versatile & timeless style
Perfect fit & feel
- Weight6.4 ounces
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.
60% polyester, 40% elastane
UA classic fit features
Pre-curved visor & structured front panels
Front panel backed with foam padding
UA microthread fabric uses
Stretch construction for a comfortable fit
- BrandUnder Armour
- Weight3.56 ounces
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.
100% raffia straw fiber
Hand wash only
Wide-brimmed straw hat
Adjustable chin strap
Quicksilver logo patch
- Weight4.8 ounces
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.
70% acrylic/30% wool
100% polyester lining
Soft, warm, and comfortable
High quality, flexible & thick
Double layered with cuffed visor
Ideal for winter outdoor sports & activities
- BrandHome Prefer
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.
100% cotton twill fabric
Wide brim for maximum sun protection
Adjustable chin strap
Available in easy wear colors
Quiksilver embroidered logo on front
- Weight6.56 ounces
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.
Shell: 60% acrylic, 40% polyester
Lining: 100% polyester
Cold-weather style generates & preserves heat
Snap adjuster secures your hat
- BrandAmazon Essentials
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.
Dry clean only
Classic 3″ brim
Self-adjustable chin cord
Mesh for cooling effect
- Weight6.4 ounces
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.
Unisex military trapper style
Quality polyester/viscose/spandex shell
Faux fur earflap & quilted lining
Windproof warm earflap & chin strap
Perfect sized brim to protect from elements
Elastic cord for better fit
- BrandJeff & Aimy
- Weight 4.97 ounces
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.
Made from insulating wool blend
Unique knit design
Classy & warm
- BrandJeff & Aimy
- Weight8.01 ounces
Men’s Hat Buying Guide & FAQ
Features to Look for in Men’s Hats
Material - What material is the most appropriate will depend on the occasion and the weather. If you're looking for a winter hat, wool or a wool blend is a must. Whether you are looking for a casual beanie hat or an elegant wide-brimmed hat, these wool blends will keep you warm but are generally breathable, too. Summer or warm weather hats are a different material altogether; they need to offer more protection from the sun while also allowing airflow. Mesh or raffia hats are a winner in these situations, but cotton will do, as well.
Style - When it comes to the best men's hats for every occasion, the different styles are almost endless. The style you choose depends on your own personal taste, but even that might change with different occasions. For a casual day or night hat, beanies and caps are fine in the winter; a baseball-style cap may be more suitable during warmer weather. If you are looking for something more formal, then a classic fedora or another wide-brimmed men's hat could be a great choice.
Face Shape - You want your hat to compliment the shape of your face rather than accentuate the features you don't love. If you are just getting into the world of hats, here are a few guidelines for styling based on the shape of your face:
- Long Face - Opt for hats that cut across the forehead, such as wide-brimmed hats or cowboy hats. Beanies may not be suitable as they may make the face look even longer.
- Round Face - Look for a hat you can wear on an angle. Wide-brimmed hats and fedoras are good for a round face. If you need to wear a beanie, pull it down as much as you can. Oversize, scrunched beanies may not be the best.
- Heart Shape - This is a very flexible face shape, and most hats are suitable for this face. However, heart-shaped faces look best in newsboy or baseball caps, as well as fedoras.
- Square Face - Soften the look of a square face with wide-brimmed hats or even floppy hats. Focus on a hat that cuts across the forehead.
- Diamond Shape - Any pull-on style hat looks good on a diamond-shaped face, so opt for pork pie or fedora style hats.
- Oval Shape - If you have an oval-shaped face, you've hit the hat-wearing lottery. This shape is almost neutral, so you can practically wear any style of hat with ease.
Head Size - A hat that is too big will sit over your head and look quite silly. A hat that is too small will look awkward and also be uncomfortable. Whenever possible, try your hat on before you make a purchase. It should fit snugly without being too tight. Otherwise, your best bet is to get an adjustable hat. You can always use a tape measure to measure the circumference of your head and check with manufacturers to find an appropriately sized hat.
Body Size - If you're a small or relatively skinny gentleman, look for a hat that isn't too wide. Otherwise, you will disappear under the hat. Along the same lines, if you are a large man, make sure your hat isn't small or flimsy; this will only make you look disproportionate.
Color - Color is important for any item of clothing. If you're wearing a casual hat for outdoor activities, a bright color is fine. However, if you're wearing a wide or medium brimmed hat for a formal occasion, a bright color will look out of place and quite tacky. Stick to somber dark colors through the winter with suits and coats; however, it is fine to wear white or lighter neutral colors during summer. You can experiment with color but keep in mind what occasion you will wear your hat at!
Men's Hat FAQ
Q: What are the different types of men's hats?
A: Hats come in dozens of different types and styles, but for the most part, they can be categorized according to the brim of the hat—or lack thereof. The basic types of hats are beanies, baseball-style caps, newsboys, fedoras, and various brimmed or brimless hats. When it comes to more formal hats, we're looking at top hats, bowlers, etc.
These days, you are more likely to be wearing a causal hat like a beanie or even a wide-brimmed sun hat. However, fedoras and pork pie-style hats are still applicable for semi-formal occasions.
Q: What men's hats are in style 2020?
A: Trendy hats for guys in 2020 include Panama style hats, as well as flat caps and fedoras. Otherwise, what is trending at the moment includes more casual, everyday hats such as baseball caps, newsboy caps, trucker hats, and a variety of beanies.
Q: What are Old Man hats called?
A: If you like the newsboy or flat cap hats, then you're looking at what is often referred to as old man hats. This hat style is synonymous with the newspaper sellers who use to stand on street corners selling this printed media. They later became popular with men all over the world, with many men wearing them in their golden years. It is quite likely your grandfather or elderly uncle had one of these hats, which is why they are associated with older gentlemen.
Q: Are snapbacks still in style?
A: One style of hat that seems to make a comeback with regularity is snapbacks. They reached the pinnacle of popularity in the 1990s but are still very much in style today. The appeal of snapbacks is that they look good on most people. Keep in mind that snapbacks are very casual, so wear them on appropriate occasions.
Q: Is it rude for a man to wear a hat indoors?
A: A true gentleman will never wear a hat indoors. While you may be able to get away with it in a lobby or foyer, once you are in the presence of other people, especially women, etiquette dictates that the hat should come off. Indoors anywhere is usually a no-no, but if you are dining out, the hat must come off upon arrival.
There are a few exceptions, though. If you are at a sporting event, it may be acceptable to leave your hat on, or if you are on public transport. The beach is an appropriate time to wear a hat constantly. Interestingly, this rule generally only applies to men, as women can leave their hats on at all times. (Their hairstyles make it more difficult to remove hats, so they get a pass.)
If you are in doubt about the appropriateness of wearing a hat indoors, the respectful and safest thing to do is to take your hat off. You will look dapper, sophisticated, and like your mother taught you well!
- Why Did Men Stop Wearing Hats - Esquire Middle East
- How Harry Rosen is Tailoring Itself to an Evolving Men's Fashion Industry - Macleans