The Best Men’s Hats To Buy Right Now

Best men's hats
Courtesy of Gym Shark

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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 haircut, and there’s a long tradition of men using hats to cover up bald spots.

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.

best hats for men 2020 Image By: BublikHaus/Shutterstock

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 winter.




You can never have too many caps, especially ones that you can work out in. This Gymshark x New Era option comes in a choice of black, navy, and grey and can keep you looking and feeling cool as it’s made out of 100% cotton and has an adjustable metal clasp at the back. Whether you’re wearing it to the gym or rocking it on the way to your local coffee shop, this men’s hat will serve you well all winter long.

GYMSHARK X NEW ERA Courtesy of Gymshark




Give some love to your head this winter with this recycled cashmere ribbed beanie from Pangaia, that’s available in an assortment of colors. Cashmere is the ultimate luxurious fabric for colder months and with gifting season here, now is your chance to make a good impression.  

Pangaia Recycled Cashmere Ribbed Beanie Courtesy of PANGAIA


3. 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.

Proud Charged black fitted baseball cap Courtesy of Proud


4. 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 when you are on vacation or live in a hot climate 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


5. 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


6. David Gandy Wellwear Heritage Cap


There is no better feeling than being confident in your own skin, which is why model and entrepreneur David Gandy is promoting the feeling of being comfortable but in true model fashion, he’s doing it in style with his brand-new Wellwear brand. The Heritage Cap is a soft and durable cotton-twill hat that is breathable for all-day wear and allows you to keep a low profile when you are avoiding the paps.

David-Gandy-Wellwear Heritage Cap Courtesy of David Gandy Wellwear




For the outdoorsy type of guy, you need more protection than the average man and so your hat needs to reflect that. Stormy Kromer is known for providing high-quality items to brave the elements and their Original Kromer cap does just that. It’s available in a range of sizes, colorways, patterns, and even has foldable earflaps. 

Stormy Kromer Orignal Kromer Cap Courtesy of AMAZON




Hurley’s cuffed beanie is a subtle nod to the beachy brand’s aesthetic and a great piece that can easily be woven into your wardrobe as a staple. This is definitely weekday friendly so feel free to have it on hand for chilly days and even chilled weekends. 

Hurley Cuffed Beanie Courtesy of AMAZON




On days when you want to be understated, reach for the Lyle and Scott Racked rib beanie. It will go with everything and adds a soft warm touch thanks to its lambswool material. If you want to up the cozy factor, wear a soft sweater and layer with an oversized puffer coat for the ultimate comfort. 

Lyle and Scott Racked rib beanie Courtesy of Lyle and Scott




Drawing inspiration from nature, the Friends With Animals brand ‘FWA’ logo hat will have everyone interested in guessing what it stands for and even more interested in you once they know it’s designed using mushrooms. Conversation starter, anyone? Team it with a casual outfit to let your hat do all the talking.

Friends With Animals ‘FWA’ logo beanie Courtesy of Mr. Porter




Brighten up your day by wearing the Acne Studios rainbow ribbed wool beanie, which is designed in muted tones that will definitely put a smile on your face every time you put it on. Who says wearing a lighter color palette is only reserved for the summer? If you are feeling brave, slip this one with an all-white outfit that will have you looking all types of heavenly.

Acne Studios rainbow ribbed wool beanie Courtesy of Mr. Porter




Been watching too many period drama boxsets and want to incorporate the golden era of dressing into your routine? Then try the Goorin Bros Pacheco for size. This traditional houndstooth design is made from pure wool and will have you reenacting the glory days in no time. 

Goorin Bros. Pacheco Wool Driving Cap Courtesy of Nordstrom


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