The Best Types of Hats for Every Type of Man

best mens hats
Courtesy of Mr Porter
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The best hats for men add an extra dollop of style to any outfit, yes, even when wearing a t-shirt and jeans. A hat worn rakishly over one eye like Idris Elba adds a touch of raffish charm, and there’s nothing wrong with that. Of course, hats can also be more practical. A stylish baseball cap can help you hide that regrettable attempt at a DIY quarantine haircut, and there’s a long tradition of men using hats to cover up bald spots.

There are many types of hats for men, and it seems like many of the best hats for men get showcased during the spring and summer months. After all, the hot weather is kind to hat lovers. Whether you’re off for a weekend of camping, hitting a festival or a party (remember those?), there’s a hat that can, ahem, top off your outfit.

Some hats, like the top hat and the boater, are reserved for specific events like weddings or Jazz-themed lawn parties. And unlike other eras, wearing the wrong hat won’t cause a riot. Yep, at one point society had loads of rules regarding men’s fashion. Gentlemen were supposed to wear straw hats in the summer and switch to woolen styles for the rest of the year. A straw hat in 1922 even caused a three-day riot in New York City, as this hilarious article in The New York Times attests.

Then there was the fiasco of John. F Kennedy’s inauguration. A reporter misspoke and stated that the president was hatless when taking the oath of office, and the next day hat sales declined dramatically. There’s a witty, well-written book that covers men’s hats, their place in society and more by Neil Steinberg, Hatless Jack: The President, The Fedora and the Death of the Hat, and it will make you laugh out loud.

But you aren’t here for a history lesson! You’re here to find the best men’s hats for your persona style. Nowadays, most guys have at least one ball cap and beanie in their closet. Celebrities like Timothée Chalamet, Idris Elba, Brad Pitt, Justin Timberlake and Tom Brady are well known for their hat game. Unlike shoes, hats don’t take up much closet space.

How To Find the Best Hats for Your Style

You can pick a hat based on your activity. If you’re running and want to keep the sun out of your eyes, a ballcap works just fine. Hiking, you’ll want a brimmed cotton hat to keep the sweat off your face, and if it has a strap, that’s a bonus, as you let the hat hang like a necklace when not in use. Straw hats also let your scalp breathe, so if you’re outside all day long, try one. With Cuban style in vogue right now, it’s a timely and comfortable look.

Most importantly, don’t be afraid to try new types of hats. It might take some trial and error to find the style that’s best for you.

What Styles of Men’s Hats Are Popular Right Now?

For Summer 2021, hats are continuing to be a pretty big thing fashion-wise right now. The three biggest hat trends for the summer, which coincidentally are the best hats for men are bucket hats, baseball caps and straw hats. When it comes to bucket hats, if you can think of a color, a pattern, a comic book character, you’ll find a matching bucket hat. They’re that ubiquitous.

When discussing the baseball hat trend, you can find them in denim (a trendy fabric for the season), and everywhere from super high-end designers to wallet-friendly deals. As with bucket hats, you can find them in everything from camo to Hawaiian prints, to retro styles, to sports teams. The baseball hat has been elevated from a basic to a must-have summer essential.

Straw Panama Fedora hats are a perennial favorite. Just as designers couldn’t stop playing with bucket and baseball caps, they started re-inventing the straw hat as a summer accessory and used everything from Amish straw hats to Aussie outback and lifeguard hats and yes, straw Cowboy and porkpie hats to freshen up men’s haberdashery. A couple of men’s designers like Ami and Fendi showed oversized hats, but if a hat can come up to your knee, would you really want to wear it? Think of those hats as more “editorial” than commuting-friendly. We’re still seeing trucker, beanies,  and dad hats hanging around too.

best hats for men 2020 Image By: BublikHaus/Shutterstock

In conclusion, it seems that guys finally have more than a few options when it comes to adding flair to what they wear. And with all those options come decisions and that leads us to our most important fashion rule:

If you like it, wear it.

Finding the Best Hats for Your Face Shape

As you would when wearing sunglasses, you need to match your hat to your head and face shape.

There are six basic face shapes: round, long, square, diamond, oval, and heart-shaped. Each face shape can wear different types of hats. You want to pick the best hats for men that complement your bone structure.

  • If you’ve got a long face, look for hats that cut across the forehead, as they shorten the face shape. Say no to beanies, but yes to wide-brimmed or cowboy hats.
  • Fedoras, flat caps, and hats worn further back on your head are fine if you have a round face. If you love beanies, wear them towards the back of your head.
  • Diamond-shaped faces tend to have a narrow jawline, so look for hats with a shallow crown like a pork pie hat, or do what round faces do, and place the hat further back on the head.
  • Heart-shaped faces should look for clipped brims like a newsboy or flat cap, fedora, ball or trucker hat.
  • If you have an oval-shaped face, you can wear anything.
  • Finally, floppy or wide-brimmed hats are great for guys with a square-shaped face, as the hats complement the bone structure instead of exaggerating it.

Now that you’ve figured out what type of hat works for you, scroll through the best hats for men this summer.


1. Norse Projects Logo-Embroidered Cotton Twill Baseball Cap


Tech, workwear, and utilitarian styles are the foundation of Norse Projects wearable separates. Cleanly, almost minimally styled, their pieces can be worn today and will look just as fresh 10 years from now. Their logo baseball cap encapsulates their ethos. Made from cotton twill, it’s embroidered with a simple “N” at the front, and that’s it.

Norse Projects Logo-Embroidered Cotton Twill Baseball Cap Courtesy of Mr Porter

Norse Projects Logo Baseball Cap



2. Two Roads Hat Co. Monterrico Palm Sun Hat – Oak


As mentioned earlier, straw hats are making a major comeback this summer. And why not? They’re a lightweight topper that goes well with a T-shirt, loose linen button down, and even an unconstructed summer suit. Two Roads’ Monterricao hat has a fedora crown (peaks nicely) and a wide brim to give you some shade. The palm straw comes from Guatemala and is made in Texas. It’s trimmed in leather and has a leather slider and chin strap.

Two Roads Hat Co. Monterrico Palm Sun Hat – Oak flat Courtesy of Two Roads Hat Co

Two Roads Hat Co. Monterrico Palm Sun Hat



3. Aviation Nation Trucker Hat


C’mon, you know you want to pop this one on. The trucker hat is one of the types of hats whose style keeps coming back. First worn in the early aughts by Ashton Kutcher, Justin Timberlake and friends, the oversized cousin of the ball cap is here for another season. California-based Aviation Nation makes clothing and accessories that are infused with the state’s surf and sand vibe. This retro-styled trucker cap encapsulates that vibe that’s so in right now.

best mens hats Courtesy of Aviation Nation

Aviation Nation Trucker Hat



4. SHEIN Raw Hem Straw Hat   


The classic porkpie hat gets updated for summer 2021 in woven straw. The raw hem adds to its rakish appeal. It would look equally sharp with a summerweight suit or a T-shirt and jeans combo. This terrifically priced hat comes four other colors: from neutral to midnight.

SHEIN Raw Hem Straw Hat Courtesy of SHEIN

SHEIN Raw Hem Straw Hat



5. Henschel Hats Aussie Breezer Cotton Mesh Hat


If you’re always hunting down the mountain path, like kayaking or anything to do with the great outdoors, plop this hat on your head. The Aussie Breezer topper adds style to a day hike and protects you against the harsh summer sun when you brunch. Made by a haberdasher who’s been creating hats since 1947, this wide-brimmed hat has a UPF rating of 50+, so it protects you against UVA and UVB rays and has a three-inch brim.

Henschel Hats Aussie Breezer Cotton Mesh Hat Courtesy of Amazon

Henschel Hats Aussie Breezer Hat



6. Nike Authentic Dri-Fit Baseball Cap


You can’t go anywhere without seeing the Nike baseball cap with the distinctive white swoosh on the front. There are many types of hats for men, but everyone gravitates towards a baseball cap, specifically the Nike ball cap. Are these the best hats for men? Well, they’re comfortable. They’ve been worn in the office, on the red carpet, and the weekends. It’s almost like it’s THE hat for guys. Made from moisture wicking materials, it can be adjusted to fit.

best hats of 2020 - Nike black dri-fit low profile swoosh baseball cap Amazon


7. Devil-Dog Dungarees Reversible Bucket Hat


And now a bucket hat that gives you two totally different looks. You can wear it either as a solid black bucket hat or show off the camo print.

Devil-Dog Dungarees Reversible Bucket Hat Courtesy of Devil-Dogs Dungarees

Devil-Dog Dungarees Reversible Bucket Hat



8. Proud Be Charged Fitted Baseball Cap


This baseball cap is one of the most common types of hats for men. This is also one of the best hats for men as it’s made for performance. The side vents cool the scalp and help dry off sweat — particularly important when you’re playing for a long time under a burning hot sun. Spotted on top of Jason Derulo’s head, this hat is made from a cotton blend, it can be tossed in the washing machine. Even better, 10% of your purchase (pre-tax) will go to the charity of your choice: St. Jude Children’s Research Hospital, Pink Ribbon Girls, Baby2Baby, Off The Street Club or the Rezvan Foundation.

best hats for men - Proud Charged black fitted baseball cap Proud

Proud Be Charged Fitted Baseball Cap



9. Sunday Afternoons Havana Cream Hat


There are hats, and then there are hats. There are certain types of hats that in seconds dress up an outfit, so if you’re traveling you won’t have to turn down a slightly fancy but fun cocktail party.  This is one of the best hats for men because it does just that. With a two-inch brim, this fedora can be folded for travel; it won’t take up room in your carry-on. If you have an event on your calendar, wearing this hat with light colored trousers and a button down shirt instantly elevates your style. The inside of the hat has a Velcro band so you can get an almost bespoke fit. The Havana Hat has a UPF 50+ sun protection built-in, so you’re looking good while protecting your skin against sun damage. It also comes in black and tan.

best men's hats 2020 - Sunday Afternoons Havana Straw Hat Amazon

Sunday Afternoons Havana Cream Hat



10. The Hat Depot Low Profile Dad Hat


What is a dad hat? Glad you asked. A dad hat is a ball cap with six panels and looks like dads everywhere will toss one on to mow the lawn, hit the lumberyard and watch T-ball. The Hat Depot makes their dad hats with 100% pigment-dyed cotton. They have a low profile, are unisex and comes in a boggling 18 solid colors and 22 color combinations.

The Hat Depot cotton dad hat Amazon

The Hat Depot 100% Cotton Pigment Dyed Low Profile Dad Hat Six Panel Cap (Pigment Blue)



11. Solbari Torquay Fedora UPF+50


Sunscreen’s become part of our skincare routine. Now more than ever, we’re taking preventative measures against sun damage and pre-mature aging, so a hat that offers sun protection is a no-brainer. Not only does this fedora protect your skin, but it also looks very cool on your head. Made from Australian wool that has a UPF+ sun protection rating, it has a cotton sweatband. The Torquay fedora comes in two other colors, black and claret.

Solbari Torquay Fedora UPF+50 Courtesy of Solbari

Solbari Torquay Fedora UPF+50



12. Brooks Brothers Panama Hat


You can’t have a summer hat roundup and not include the Panama Hat. It’s a classic summer accessory. Interestingly enough, the first Panama hats were constructed during the 17th century in Ecuador. During the mid-1800s there was a gold rush in Panama, an enterprising haberdasher imported the Ecuadorian hats and the miners re-named them the “Panama Hat.” Teddy Roosevelt wore one during the building of the Panama Canal and that’s how the hat got its place in history and on heads. Brooks Brothers’ version of the Panama switches out the classic black band and replaces it with a jaunty madras print.

Brooks Brothers Panama Hat Brooks Brothers

Brooks Brothers Straw Panana Hat



13. Goodfellow & Co Khaki Boonie Hat


Could this be the summer that Aussie hat styles rival the bucket hat? Welp, there’s quite a few Aussie-influenced toppers to choose from out there. Goodfellow & Co’s Boonie hat is made from a stretchy cotton knit; it’s breathable and comfortable. It has an adjustable neck cord, so it won’t get blown off on windy days.

Goodfellow & Co Khaki Boonie Hat Courtesy of Target

Goodfellow & Co Khaki Boonie Hat



14. Diop Akira Bucket Hat


We’ve covered Diop hats before, and we’re highlighting them again as they’re so cool. Founded in Detroit, this Black-owned brand uses Ankara fabric to create their cotton bucket hats. The Akira bucket hat uses pink, navy, black and white in an overlapping geometric print.

Diop Akira Bucket Hat Courtesy of Diop

Diop Akira Bucket Hat



15. Neighborhood Dusters Printed Bucket Hat


Neighborhood’s oversized hat is an oversized hat that you can wear on the street and the trail. Based on the bucket hat style, this cotton and nylon mesh paneled piece has an oversized brim that has an extended back that can fold down and be used as sun protection. The hat also has an adjustable drawcord that can be used to create the perfect fit.

Neighborhood Dusters Printed Mesh-Paneled Cotton and Nylon Blend Bucket Hat Courtesy of Mr Porter

Neighborhood Dusters Bucket Hat



16. Treasure & Bond Oversize Bucket Hat


Looking a bit like a cross between a fisherman and a bucket hat, Treasure & Bond’s denim bucket has a wide-ish brim, well a tad wider than the traditional bucket hat. It mines both the denim and the frayed hat trends.

Treasure & Bond Oversize Bucket Hat Courtesy of Nordstrom

Treasure & Bond Oversize Bucket Hat



17. H&M Denim Cap


No matter what the season, you can never go wrong with the classic baseball cap. If you want to be on-trend and stay on-budget, you can’t go wrong with this very wallet friendly cotton cap.

H&M Denim Cap Courtesy of H&M

H&M Denim Cap



18. Halogen Patterned Straw Fedora


This geo print is eye candy. The unisex straw fedora has a fabric ribbon around the crown and the pattern could really set off an all-black or all white outfit. It’s a touch dandy and a touch fashion forward.

Halogen Patterned Straw Fedora Courtesy of Nordstrom

Halogen Patterned Straw Fedora



19. By Walid Callum Upcycled Patchwork Cotton Bucket Hat


Patchwork patterned hats are a big summer trend this year. This cotton bucket hat is at the same time a tad formal, fashionable and slightly whimsical. Try it with a linen button down, chinos and slip-ons. Another way to wear it is with a lightweight blazer, polo shirt and jeans.

By Walid Callum Upcycled Patchwork Cotton Bucket Hat Courtesy of Matches Fashion

By Walid Callum Cotton Bucket Hat



20. SHEIN Men’s Fedora Hat


Not every fashion accessory needs to be an investment item. Toying with the idea of wearing a fedora or a hat in general this summer, then look at this neatly styled fedora as a hat with training wheels. The price won’t set you back as you spread your style wings.

SHEIN Men Fedora Hat Courtesy of SHEIN

SHEIN Men's Fedora Hat



21. Hairbrella HB Elements Unisex Docker Hat


Beanies, like ball caps, are hats that can be worn all year long. What’s special about this one is that it’s (a) waterproof, and (b) lined in satin. It protects your hair inside and from the elements at the same time. Try it with a Breton shirt and dark jeans.

Hairbrella Unisex Docker Hat Courtesy of Hairbrella

Hairbrella HB Elements Unisex Docker Hat



22. Ariat Twisted Weave Cowboy Hat


Cowboy anything never goes out of style. That said, Ariat’s known for their well-crafted boots, but most of us didn’t know that they also made cowboy hats with reasonable price points. This open weave cowboy hat is an easy hat to wear with any of your casual or athleisurewear items.

Ariat Twisted Weave Cowboy Hat Courtesy of Amazon

Ariat Twisted Weave Cowboy Hat



23. Gucci Original GG Canvas Baseball Hat


Logomania is a trend that is slowly easing its way into every day fashion, much like it did in the late 70s. This sleek black ball cap from Gucci is done in a tonal monogram with the luxury house’s iconic stripe at the back.

Gucci Original GG Canvas Baseball Hat With Web Courtesy of FarFetch

Gucci Original GG Canvas Baseball Hat



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