The 17 Most Stylish Types of Mens Hats

Hats have cemented themselves as eternally stylish men’s accessories. From baseball caps to bucket hats, fedoras to snapbacks, men’s hats are a versatile, functional, and stylish addition to any look. They’re also practical and suitable for any season. Rain, hail, shine, or snow, a hat will keep you warm, dry, and sheltered from the sun all while looking great. On top of that, hats can finish off any casual, classy, or eclectic ensemble in a simple yet inspired way. Here are the best men’s hat styles you need to know today.

15 Types of Hats: Men’s Hat Styles To Know

Hats have cemented themselves as eternally stylish men’s accessories. From baseball caps to bucket hats, fedoras to snapbacks, men’s hats are a versatile, functional, and stylish addition to any look. They’re also practical and suitable for any season. Rain, hail, shine, or snow, a hat will keep you warm, dry, and sheltered from the sun all while looking great. On top of that, hats can finish off any casual, classy, or eclectic ensemble in a simple yet inspired way. Here are the best men’s hat styles you need to know today.

1. Snapback

The ’90s style baseball cap burst onto the fashion scene after the New York snapback became increasingly popular with Yankees fans. Nowadays, snapbacks have cornered the market, being worn by cap connoisseurs, ballers, fashionistas, and cool kids all over the world. The name comes from the hat’s adjustable fastener at the back. Like its vintage cousin, the dad hat, it is also one-size-fits-all, providing a relaxed, oversized fit. However, the snapback is more rigid in its design, making it more structured. Snapbacks add an effortless yet instantly cool vibe to any outfit.

2. Beanie

Once a mere winter essential, beanies have become genuinely timeless and trans-seasonal pieces. While you might not want to wear one in the middle of summer, you can pretty much rock a beanie from winter to spring. They go with a lot of styles and can easily take you from streetwear to sleek wear. These nifty knitted accessories can keep your head warm and your style hot. From chunky knitted winter woollies to stylish slouchy pieces, beanies are super versatile. We’d recommend going for one made of thin material and in a neutral color like navy or grey. This way, you can get the most wear out of it.

3. Trucker Hat

First appearing in the ’70s, the trucker hat is one of the most popular hat choices today. With a peaked cap and a close-fit crown, it protects you from the sun while being casual enough for everyday wear. There are endless colors and designs to choose from, some featuring brand and sports team logos, symbols and prints. Wear it in laid-back events, such as hanging with your friends or going for a midday walk.

4. Fedora

Love it or hate it, the Fedora has stood the test of time. Going from the hat of choice for gangsters in the 1920s and 1950s to a hipster staple item in the 2000s, Fedoras is probably one of the most polarising men’s accessories. Today the felt firm-brimmed hat is once again on-trend and a fantastic wardrobe addition. Although fedoras come in various sizes and colors, we’d suggest sticking to those with more neutral tones and medium widths.

5. Trilby

Despite often being confused with a fedora, a trilby is a different type of hat. Made from tweed or straw, the Trilby features a smaller brim and taller crown than the fedora, meaning you can wear it from spring to autumn. Wear the trilby at the back of your head, instead of pulled forward to protect your face. It is a statement fashion piece rather than a functional hat. They are the hats of choice for boy band members, such as Justin Timberlake, as well as members of the upper class, and are frequently spotted at horse racing events around the world.

6. Panama Hat

A Panama hat is perfect when paired with a beach backdrop and a white linen shirt. This traditional brimmed straw hat hails from Ecuador and will have you looking as hot as a Miami summer. Made from plaited leaves, the Panama hat has become a must-have accessory for seaside and tropical destinations. Panamas are made for sunshine and blue skies, so don’t try to rock this hat in winter. They are light in color and weight, breathable, easy to wear, and faultlessly fit with a laid-back beach style.

7. Bowler

The bowler hat is one of the most iconic items of British style, made famous by notable actors such as Charlie Chaplin, Curly Howard, and John Cleese. It is a hard, felt hat with a narrow brim and is also commonly known as a derby. This hat is a favorite of the upper, middle, and working class alike, but we would steer clear of wearing it casually. Try out this trend with double-breasted suits, tailored pants, dress shoes, a vintage Corvette, or a British accent. That type of thing.

8. Dad Hat

While your dorky dad might not seem like someone to take fashion advice from, dad hats are awesome vintage accessories that scream laid-back style. These relaxed baseball caps are usually canvas or cotton with a slightly curved brim. The dad hat also sports an adjustable strapback closure, making it one-size-fits-all. Dad hats make great additions to any sports-luxe ensemble and can be used to add a vintage twist to any casual look.

9. Newsboy

Emerging in the 19th century, these old-school caps have made a big comeback in the 2000s. A newsboy hat is similar to a flat cap. These round and full caps have panels and a button on top, attaching the front of the hat to the brim. Gracing the heads of many affluent men and women, fashion houses have embraced traditional men’s caps. Many high street retailers also stock newsboy or baker boy caps.

10. Flat Cap

Popular among celebrities and television characters, flat caps come from humble roots. The flat cap was once typically worn by chimney sweepers and farmers. These stylish pieces of headwear come in wool, tweed or cotton. For extra warmth and comfort, these stiff-brimmed rounded caps are lined. Flat caps look best when paired with a smart casual style for a touch of charm.

11. Bucket Hat

Bucket hats are back, and the ’90s revival continues with no sign of stopping. Gaining popularity with various musical and skater subcultures, the bucket hat has gone from a humble fisherman’s hat to downright cool. Made from heavy-duty cotton fabrics such as denim and canvas, or wool blends like tweed, bucket hats feature wide, downward-sloping brims, resembling an inverted bucket. They have been a street style favorite for years and are perfect when trying to create a laid-back urban look. To rock the look, try throwing on a bucket hat with a bomber jacket, high tops, or even a jersey.

12. Baseball Cap

From snapbacks to dad hats, there are so many variations of baseball caps, but you can never go past a classic. Baseball caps started off as simple five-panel caps with adjustable straps and were worn as part of baseball team uniforms. Today, they are as much a fashion item as a piece of sportswear. A favorite of street style stars and celebrities, the baseball cap has graduated to an iconic status because of its simple and cool designs.

13. Trapper Hat

Warm, stylish and retro, a trapper hat should be on your winter must-haves list. Made from sheepskin suede with leather trim, trapper hats come in a variety of real and faux fur options. Modern editions of the trapper hat are available in a selection of plaids, corduroy, and various waterproof materials. These hats scream adventure and are perfect for the outdoorsman. Try rocking a flannelette shirt and blue jeans with this hat trend, instead of a shirt and tie.

14. Boater

The boater is another summer essential when it comes to men’s headwear. This stiff straw hat with a grosgrain ribbon around its crown peaked in popularity in the early 20th century. Often worn by barbershop quartets and in period dramas, they are now a rare sartorial sight. A boater hat is ideal if you’re looking to make a splash on the fashion scene this summer. They are a fun, chic, and original alternative to the Panama hat or a fedora. These flat-topped, wide-brimmed straw hats are definitely due for a comeback.

15. Pork Pie

After it became a recurring accessory on Breaking Bad, the pork pie grew increasingly popular. The men’s hat was one of the most popular in the 19th century. Today, hipsters mostly wear the pork pie style, which features a cylindrical crown. It also has a flat top that is pinched around the outer edge. These hats provide a classy, modern, and artistic aesthetic.

16. Visor

Typically seen in golf and tennis, the visor is a great accessory to keep the sun out of your eyes. This headwear features a peaked cap but doesn’t have a crown to secure it on the head. Instead, it includes a band above the ears – this can help stop sweat from entering the eyes while you work out. his is best suited for outdoor activities that need sun protection but isn’t too heavy to become distracting.

17. Cowboy Hat

For centuries, the cowboy hat has been a staple in Mexico and the US history and culture. With a wide brim and a high crown, this headwear is suited to outdoor activities in dry and hot environments. While you would normally see these with a pair of jeans and western boots, you can style them with almost any casual outfit.

18. Homburg

The Homburg hat is a semi-formal accessory that is often compared to a fedora. With a high crown and a dent running down the middle, it is usually made from felt and in a dark shade. It was originally worn during hunting excursions, but it became a popular choice by the likes of Sir Winton Churchill and Al Pacino in The Godfather.

19. Boonie Hat

The Boonie hat is a popular choice for outdoor activities, especially in tropical climates. Originally intended for the army, it features a bucket hat silhouette with a wide brim. It’s usually made from soft and floppy fabrics and an adjustable chin strap. You’ll usually find them with eyelets or mesh on the crown to provide breathability in hot environments.

20. Top Hat

There has still never been a piece of headwear as dominating or as sophisticated as the top hat. Don’t panic, we’re not suggesting you need to go Abe Lincoln style, but a shorter, stylish top hat will undoubtedly make you stand out in a crowd. These tall, flat-crowned, broad-brimmed hats were once the height of high-class dressing, but today they are a rarity. If you’re looking for a fun and fancy way to class up your next formal event, why not try a top hat?

How to Choose Men’s Hat Style

Styles

There are many different hat styles for men to try. Depending on the event and season you are in, you can try something that suits you and your needs. For casual occasions, try something laidback like a baseball cap. You can usually find something plain in color but featuring a large icon or logo on the front to express your personality. Other popular hat styles include beanies and trapper hats – they’re especially popular in colder months and match a wide variety of clothes and accessories. For formal events, try styles such as a pork pie, trilby or Homburg. However, if you are going outside and need solid protection from the sun, we recommend a Boonie or bucket hat.

Season

During warm temperatures, your priority should be protecting your face and neck from the harsh rays of the sun. Popular choices in summer include baseball caps, bucket hats, and anything with a wide brim to shield your features from the light. During cooler months, the need to shy from the sun is reduced, but you need to stay warm. That’s where headwear like beanies and trapper hats come in. They will fit snugly on your head and trap the warmth close to you – find something that covers your ears and forehead for maximum protection from the elements. In tropical conditions, it’s best to wear a hat that has a wide brain and is made from breathable fabrics – Boonie hats usually include mesh inserts and eyelets to let the air regulate throughout your scalp.

Occasion

Certain hats are made for specific occasions. While it was once popular to wear a fedora or trilby hat to the office and semi-formal occasions, you’re less likely to see it today. Instead, the high-crown headwear is best-suited to formal and semi-formal occasions like an outdoor wedding. Save beanies, caps, and bucket hats for casual and laid-back events – they look best with jeans, chinos, and other relaxed garments.

Face Shape

Unsure what hat suits you best? First, determine what face shape you have. Round faces look best with a high crown, as it balances out the height of your head without making you look too wide. We recommend trying a fedora or trilby – it’s a flattering and timeless choice for semi-formal occasions and looks great in any season. Heart-shaped faces look best in cowboy and boater hats – they sit perfectly on your forehead, creating symmetry with a pointy chin. Plus, the smaller brim will keep the width of your face in proportion with the rest of your features. Newsboy caps look great on those with a square-shaped face, as they soften any hard features, such as your jawline. For those with an oblong face, you can wear pretty much anything you like – lucky!

Type of Hats FAQs

What are the different types of mens hats?

The different type of hat styles includes the Fedora, Triby, Panama Hat, Bowler, Snapback, Dad Hat, Newsboy, Flat Cap, Top Hat, Porkie Pie, Boater, Baseball Cap, Bucket Hat, and Beanie.

What men’s hats are in style 2020?

The biggest trending hats for men in 2020 include bucket hats, beanies, snapbacks, Fedora, Panama hats, and flat caps.

What are Old Man hats called?

Generally, if you’re talking about an “Old Man” hat, then you’d be referring to a flat cap or newsboy style. These have seen a huge resurgence in popularity thanks to television shows like Peaky Blinders.

What is a peaky Blinder cap?

A Peaky Blinder cap is a flat cap or newsboy style hat. The style has recently become very popular again thanks to the television show Peaky Blinders, about a Birmingham gang in the early 1900s.

Who started the bucket hat trend?

Bucket hats have spent time in the limelight a couple of times over the past 100 years. Farmers and fishermen initially used them as a protective piece of clothing, then they were military-issued attire in the 60s and 70s. Bucket hats then found popularity in the hip-hop and rap scene in the 80s and 90s, but since then, they have been out of favor. That was until the mid-2010s when Melissa Forde released a line in 2015, and they then became a hit for SS2018. Brands like Fenty and Puma, Michael Kors, and Karl Lagerfeld for Chanel put them on the runway, followed by Lanvin and Valentino. The latest resurgence ties in with other 90s revival styles, such as scrunchies, over-sized t-shirts, and bandanas.

Are snapbacks still in style?

While snapbacks fell out of fashion for a little while, this 90s iconic is well and truly back in style. To create a modern, up-to-date look, pair it with a white shirt, chinos, and pair of Converse. Alternatively, don a graphic tee, ripped jeans, and hightops for a new take on the hip-hop look.

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The 17 Most Stylish Types of Mens Hats

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 Mens Hat Styles

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

A hard felt hat, an Akubra is a sort of Australian cowboy hat that dates back to late 19th century Tasmania.

It’s still warn for sun protection by many Australians today, particularly in rural areas.

Reminiscent of the iconic hat Paul Hogan wore in Crocodile Dundee, it works on just about any face shape and gives off a distinctly rugged bad-ass vibe.

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 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

The baseball hat started with an obviously practical purpose – to keep the sun out of ball players’ eyes while they fielded fly balls.

But it’s developed an additional aesthetic one – to add a dose of athletic, casual cool to the head of just about any man.

And I do mean any man. Baseball caps have developed a bit of a reputation as “dad hats,” but they look just as good on guys without a brood of their own.

Toque (aka Beanie)

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 or beanies.

No matter what you call them, these knit winter hats are an absolute staple during colder months.

They’re a more portable alternative to the trapper hat made famous by movies like Fargo, since they’re easy to fold up and shove in the pocket of your winter jacket.

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

As their name implies, straw hats like the Boater 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

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 the bucket hat – also sometimes called a sun hat – is back in a big way, and a popular choice among stylish members of Gen Z.

Fedora

Both a classic style of men’s hats and (in my opinion) one of the most stylish, the Fedora has gone from one of the most popular hats 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 dashing while doing so, the theory goes, that millions of men decided they should ditch their hats as well.

As a result, the Fedora and other similar dress hats, like the panama hat, have been on the decline ever since.

(Although, at Joe Biden’s inauguration in January 2021, 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

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)

Similar in design to a flat cap (and often confused for one), newsboy caps share the stiff front visor, but have a rounder and fuller shape.

A newsboy hat is often made of multiple panels that come together at the top of the hat, where they’re held in place with a button, making it a more floppy hat than the flat cap.

Like flat caps, they’ve 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.

| Related:

• Want to learn how to rock another staple of Thomas Shelby’s (stylish as hell) wardrobe? Check out our guide on how to wear rock a pocket watch in the 21st century.
• And if you want to know how to suit up like a Shelby, check out our full roundup of the best Peaky Blinder suits available to buy online.

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.

Its German origins are actually a bit 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

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 Pork pie 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)

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:

It has a similar shape up top, but a much wider stiff brim, which is designed to protect against your face on sunny days.

Top Hat

Easily the most formal of all the different hat styles 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 formal occasions when the dress code calls for a morning suit, like at certain horse races.

Trilby Hat

Easily the hat that’s most often confused with a Fedora (thanks for nothing, Justin Timberlake) entire articles have been written about the difference between a Trilby and a Fedora, but ultimately it comes down to the brim.

The Trilby sports a much more narrow, short brim, which is angled so that it dips down at the front and goes up at the back.

By contrast, the Fedora’s brim 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 hat, but in most cases he actually opted for the thin-brimmed Trilby.

Trucker Hat

What do you get when you take a classic baseball cap and remove the fine materials and craftsmanship? Trucker caps.

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.

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 Mens Hats

Now Learn How to Look Your Best From the Head Down

Now that you understand what distinguishes the different types of hats for men, 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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About Dave Bowden

Irreverent Gent founder Dave Bowden is a style blogger whose advice on how to look good and live well has been featured in some of the world’s most trusted publications, including New York Magazine, The Wall Street Journal, Business Insider and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto’s sports teams.

Check out Dave’s Style Story to find out how a chance encounter with his friend’s step-dad taught him the value of looking good and living well. (Don’t worry—it’s less creepy than it sounds!)

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