The Best Fedoras To Wear in 2021 for Gentlemanly Charm

best mens fedoras
Courtesy of @stetsonusa

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Out of all the fashion accessories you can wear, hats are easily the most practical and helpful of the bunch. Capable of blocking the sun on a bright day, helping you hide a thinning head or covering your hair if you’re having a bad hair day or are too lazy to style, hats should not go overlooked. Regardless of why you choose to wear a hat, it’s a stylish way of quite literally topping off an outfit. However, ball caps aren’t often the most stylish or appropriate choice. That’s why it might make sense to reach for something that’s a little nicer — which is where finding a great men’s fedora hat comes into play.

Fedoras, in some corners of the Internet, get a bad rep. But the key to making your fedora look cool is opting for a wider silhouette. Wide-brimmed fedoras have more in common with cowboy hats of yesteryear than anything else, making them a clean and sophisticated way of elevating any look. Think of wearing your fedora in the same way that a cowpoke might, with your best denim and a killer jacket. Regardless of how you choose to wear it, we’ve rounded up some of the best fedora hats on the market. So saddle up, slip one on, and ride out knowing that you’re looking you’re best.


1. Brixton Messer II Felted Wool Fedora


With its rich cognac color, this wool men’s fedora from Brixton makes for a clean addition to any outfit. It is offset by a rugged leather band that ties the whole hat together in a classically stylish package and will look damn good with almost anything you rock. It’s one of the brand’s classic offerings, boasting a stiff brim that provides a solid structure. While it’s not as inherently packable as some of the other options on this list, its sturdy construction makes it the king among even the most stylish fedoras on this list.

Read More: The Best Men’s Hats

Brixton Messer II Felted Wool Fedora Courtesy of Nordstrom


2. Stetson Cromwell Crushable Fedora


Stetson has been the maker of quality hats since the late 1800s (!), so they know a thing or two crafting a suitable wide-brim fedora hat. The Cromwell model is made from crushable wool that will regulate your body temperature while also providing a stylish option for your dome. Garnished with a stylish leather band and metal Stetson-branded button, pair it with a full jean ensemble to unleash your inner yee-haw energy.

Stetson Cromwell Crushable Fedora Hat Courtesy of Amazon


3. Pendleton Indiana Fedora


You guessed correctly: The “Indiana” in the name of this hat from Pendleton comes from none other than the titular Indiana Jones himself. Modeled after his classic hat, this fedora is a wide-brim offering that’s crafted in a darker hue for use with all kinds of climates and outfits. In addition to being made from an easy-to-pack wool material, the hat also been treated with a material to make it slightly water-resistant should you happen to get caught in the rain.

Indiana Fedora hat Courtesy of Amazon


4. Lisianthus Wide Brim Fedora Hat


Want to be stylish on a budget? Heck, who doesn’t? Well, with this fine-looking fedora from Lisianthus, you can. The cotton/polyester blend hat is available in a wide range of colors, making it easy for your to match your hat to your outfit or emotions, if you so choose. We especially like the felt-like look of this hat. It just feels so dang dapper.

Lisianthus Men & Women Vintage Wide Brim Fedora Hat Courtesy of Amazon


5. Pineapple & Star Genoa Fedora Straw Hat


This packable straw fedora hat is great for the beach and warm weather. It’s designed with UPF 50+ paper straw and polyester to block out harmful rays and it comes with an inner size-adjustable system and detachable chin cord strap for the perfect fit.

Read More: The Best Sun Hats for Men

Pineapple&Star Genoa Fedora Bucket Sun Straw Beach Hat Courtesy of Amazon


6. Scala Classico Crushable Wool Felt Fedora


If all black worked for Johnny Cash, it’ll work for you. This fedora hat from Scala will let you channel your inner Westworld should you so desire, or just work to pair off a sturdy winter ensemble. With its wool construction, it’ll keep you warm too. This style is crushable and packable so you can take it with you everywhere you go.

Scala Classico Men's Crushable Wool Felt Fedora Courtesy of Amazon


7. Bailey of Hollywood Tino Fedora Trilby Hat


While most of the hats we’ve featured here tend to edge more towards the wider-brim style of fedora, this version from Bailey of Hollywood is more of the traditional style. This shorter style is made in taupe brown wool that’s easy to work into any outfit. The included feathers add character to this already sophisticated style.

Bailey of Hollywood Men's Tino Fedora Trilby Hat Courtesy of Amazon


8. Filson Tin Packer Canvas Fedora


Wool might be too tough of a material for some, so having a hat crafted from a durable canvas like this one from Filson is a good alternative. As sort of a cross between a standard fedora and a bucket hat, this Tin Packer is a bit rounder in style. The benefit of having the canvas though is to provide some protection from not only rain but to make it really packable. Perfect for outdoor wear (i.e., hiking) it’s only going to get better looking the more the canvas gets broken in.

Filson Tin Packer Canvas Fedora Courtesy of REI


9. Bailey of Hollywood Fedora


If you’re looking for a fedora you can wear for extended periods of time without it getting too sweaty or uncomfortable, this selection from Bailey of Hollywood is your best bet. Inside the interior of the hat is a padded comfort sweatband that helps to wick moisture away so your brow doesn’t get too sweaty, while also resting in such a way that it almost feels like it isn’t there. Plus, there are a variety of different colors available, so you can find a version that best suits your individual style.

Bailey of Hollywood Fedora Hat Courtesy of Amazon


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