The 17 Most Stylish Types of Mens Hats

Dave Bowden

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If you’ve ever gone looking for the right headgear to elevate your look, you’ve probably noticed that there are roughly a gazillion different types of men’s hats.

(Alright fine, that’s not a scientifically accurate number – or even a real one – but that’s definitely how it feels sometimes.)

But while there may be a wide range of men’s hat styles in existence, the truth is that, for the modern man, there are really only a select few in play if you want to look your best.

From formal-feeling wide brim hats to cool, casual knit caps, in this post I’ll break down some of the most classic, masculine and stylish types of hats for men who want their lid to look sharp.

The Most Essential Types of Mens Hats

Breaking Down the Most Stylish Types of Hats for Men

Ascot Cap

Also called a Cuffley cap or Lippincott cap, the Ascot has a rounded shape in both the front and back, and a certain hardness that helps it maintain its shape.

Ascot Cap vs Flat Cap

The Ascot is often mistaken for the flat cap (on which, more below), which is similar in overall style. But unlike ascots, flat caps don’t have the same round, almost bulbous shape; as their name implies, flat caps lie flatter on the head.


Akubra Hat

Image via Akubra Hats on Instagram

An Akubra is a sort of Australian cowboy hat that dates back to 1870s Tasmania, and is still warn by many Australians today, particularly in rural areas. It gives off a distinctly rugged bad-ass vibe, and is reminiscent of the iconic hat Paul Hogan wore in Crocodile Dundee.

The name is actually derived from the company that first made and popularized them, so it’s sort of like the Kleenex of the hat world. (And yes, I admit that it might seem paradoxical to refer to the same hat as “rugged bad-ass” in one sentence and “the Keelnex of the hat word” in the next, but here we are.)


Balaclava

The Balaclava says “Give me your wallet” but the eyes say “Honestly, it’s insecurity that drives me to mug people. I guess it all started with my mother…”

The perfect head gear for both hitting the slopes and robbing a bank* (talk about versatile!) the Balaclava is not so much a hat as a mask.

More specifically, it’s a knitted winter hat/ski mask that can be rolled up to protect the top of the head, or rolled down to protect the entire face, with holes for the eyes and mouth.

The (rather bad-ass sounding) name is derived from the Battle of Balaclava, a Crimean War battle from 1854 in which British troops wore handmade knitted headwear in attempt to protect themselves against the harsh winter weather.

*I really can’t stress this enough: that was a joke.
Please don’t rob a bank! 


Baseball Cap

Could I have found more athletic baseball cap shots? Of course. Could I have found a more stylish shot? Never. (Screenshot via Omaze on YouTube)

Baseball caps started with an obviously practical purpose – to keep the sun out of ball players’ eyes while they fielded fly balls – but have developed an additional aesthetic one – to add a dose of athletic, casual cool to the head of just about any man.


Toque (aka Beanie)

Statham made a toque look manly in 2008’s The Bank Job, but to be fair, he didn’t exactly have to worry about messing up his hair

What we Canadians call toques (the spelling is derived from a French word, but in English it rhymes with “nukes”), Americans tend to refer to as knit caps, which is descriptive if not exactly imaginative, or even worse, beanies, which is just plain silly sounding.

No matter what you call them, these knit winter hats are an absolute staple during colder months. While there’s no more stylish way to keep your head warm when the temperature drops, the one disadvantage is that they tend to mess up a man’s haircut, so consider yourself warned.


Boater Hat

No, this isn’t Billy Nye rocking an Instagram filter; it’s former MLB manager Connie Mack rocking a Boater hat in 1911

As their name implies, straw Boater hats were the headgear of choice for seamen in the late 1800s and early 1900s.

But today they’ve also come to be associated with barbershop quartets, which came into popularity at about the same time.

Today you most often see boaters back in warm-weather and nautical settings like regattas or garden parties (assuming you’re the type of person who attends regattas and garden parties, that is).


Bowler Hat

Bowler hat image: via the Peloponnesian Folklore Foundation on Wikimedia

Also known as a Derby hat, bowlers hats have a rounded crown and a famously bulbous shape that’s more spherical than most other hats.

They were originally created in London in 1849 (by a pair of brothers named Bowler, hence the name), but gained traction in the United States, becoming the most-worn style of hat in the American West.

Since then Bowler has popped up in many forms of media and pop culture over the years, from Charlie Chaplin and Oddjob to Boy George and the Riddler.


Bucket Hat

A soft cotton hat with a wide brim that protects your face and neck from the sun, the Bucket hat was first made famous by Gilligan on Gilligan’s Island, and has gone in and out of fashion ever since.

It had something of a resurgence in the ’90s when the lead singer of the New Radicals wore one in their video for You Get What You Give.

Of course, today we live in an era when everything ’90s is in again (I’m looking at you, circular sunglass lenses), so it’s no surprise that bucket hats are back in a big way.


Fedora

David Gandy (looking dapper as hell) in a Fedora shot via Conor Clinch on Wikimedia

Both one of the most classic types of men’s hat and (in my opinion) one of the most stylish, the Fedora has gone from a staple on the heads of most men to something of a novelty.

Why? According to a popular menswear myth, it was all JFK’s fault. When John F. Kennedy was inaugurated in 1961, at the height of the Fedora’s popularity, he famously chose to forego the hat.

And he looked so damn dapper and dashing while doing so, the theory goes, that millions of men decided they should ditch their hats as well, and the Fedora has been on the decline ever since.

(Although, as I watched Joe Biden’s inauguration, I couldn’t help but notice that more men than I would have expected were actually sporting Fedoras in the crowd, so maybe it’s finally on its way back? Fingers crossed.)


Flat Cap

Brad Pitt rocked a Flat Cap in The Curious Case of Benjamin Button, and liked it so much that he continued wearing it in his personal life for years

The Flat cap goes by more names than maybe any other type of hat.

In Ireland, where it originated, it’s known as a paddy cap, in Scotland they call it a bunnet, in Wales it’s a Dai cap, while in New Zealand it’s (for some reason) called a cheese-cutter and in the U.S. it’s just called a driving cap.

The traditional flat cap is made of tweed (which is no surprise, given its Irish heritage), but you can also find them in wool, cotton and more out-there materials like leather and linen.


Newsboy Cap (aka a Gatsby)

Cillian Murphy’s Thomas Shelby character in Peaky Blinders has helped usher in a newfound appreciation for the Newsboy cap

Similar in design to a flat cap (and often confused for one), the Newsboy cap shares the stiff front visor, but has a rounder and fuller shape.

It’s often made of multiple panels that come together at the top of the hat, where they’re held in place with a button.

Like Flat caps they’re seen something of a resurgence in recent years, due in no small part to the popularity of shows like Peaky Blinders, where they’re worn to perfection by Cillian Murphy and his co-stars.

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Homburg Hat

Sometimes confused with a Fedora, a Homburg is another style of felt hat that has a brim running all the way around it. But unlike a Fedora, a Homburg has just one single dent at the top, called the gutter crown, which runs the length of the hat.

The name comes from the German town where the hat originated as hunting gear, which is somewhat ironic because it’s probably most recognizable as the preferred hat style of Winston Churchill, the British Prime Minister whose crowning achievement was rallying the Brits to strengthen their resolve and defeat the Germans in the Second World War.


Porkpie Hat

Sorry, Frosty: the most famous Porkpie sat atop the head of the man called Heisenberg

Another felt hat that’s in the same vein as hats like the Fedora and Homburg, the Porkpie is distinguished by its flat top and circular shape, which resembled an actual pork pie, hence the name.

Like the Boater, Porkpies were most popular in the early 1900s and peaked during the Depression. And though it’s name-dropped in Frosty the Snowman, the most famous modern Porkpie hat sat atop the head of Bryan Cranston’s Walter White character in Breaking Bad, when he took on his deadly meth-cooking persona, Heisenberg.

(And it’s a testament to just how amazing an actor Cranston is that he managed to look menacing as hell in the Porkpie.)


Cowboy Hat (aka a Stetson)

It can be hard to pull off a Cowboy hat in modern times (especially in urban settings), but Timothy Olyphant made it work in Justified

What we now think of as a Cowboy Hat was for a longtime simply known as a Stetson, named for the eponymous company founded by John B. Stetson in 1865, which essentially became the unofficial hat maker of the American West.

While there are multiple models, the most famous style of Cowboy hat almost looks like a Fedora on steroids, with a similar shape up top, but a much wider brim designed to protect against your face against the sun.


Top Hat

If you’re presenting yourself to the King of Sweden, as U.S. Ambassador Mark Brzezinski did in 2011, then a top hat makes sense; in pretty much every other scenario, not so much (photo via US Embassy on Wikimedia)

Easily the most formal hat on this list, Top hats (which are sometimes also called Beaver hats) are very rarely worn today unless as part of a costume.

The one place you may still see them in real life is in the UK, where grey Top hats (which for some reason are referred to as”white” hats) are worn to certain events when the dress code calls for a morning suit, like at certain horse races.


Trilby Hat

Though many mistake it for a Fedora, Don Draper tended to favor Trilby hats

Easily the hat that’s most often confused with a Fedora, entire articles have been written about the difference between a Trilby and a Fedora, but ultimately it comes down to the brim.

The Trily sports a much thinner brim, which is angled so that it dips down at the front and goes up at the back, whereas the Fedora’s brim, by comparison, is wider and relatively flat/level all the way around.

Mad Men’s iconic lead character Don Draper provides a great example of the differences between the two hats, and how frequently they get confused; most people automatically assume that Draper wore a Fedora, but in most cases he actually opted for the thin-brimmed Trilby.


Trucker Hat

Another hat, another Statham reference; he wore one to rugged rural perfection in 2013’s Homefront

What do you get when you take a Baseball cap and remove the fine materials and craftsmanship? A Trucker hat.

Alright fine, that’s a bit harsh, but it’s not far off. A Trucker hat is basically a baseball cap that uses foam for the front and brim, and cheap – excuse me, “breathable” – mesh for the back.

Fun Hat Fact:

Before they were adopted by long haul truckers, Trucker hats were called “gimme” hats, because they were frequently given away as part of a free promotion from farming supply companies, who gave them to farmers and truckers.


You Know the Best Types of Hats for Men

Now Learn How to Look Sharp From the Head Down

Now that you understand what distinguishes the different types of men’s hats, you’ll be able to choose the right hat style to suit your head, your look and your life.

But while the right headgear can certainly help, the truth is that handsomeness goes well beyond hats.

If you want to look your best, you don’t just need the right hat; you need to know how to optimize your entire appearance from head to toe.

Enter your email address below and I’ll send you a head-to-toe checklist that will help you do just that. It breaks down the nine most important details you need to know about, and shows you how to nail each one so you can present your best self to the world.

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Dave Bowden

About

Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a long-suffering (but very patient) Toronto sports fan and the husband of a wonderful (and thankfully even more patient) wife.

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