The Ultimate Guide To Men’s Hats


Men’s hats  – while born out of practical necessity, often evolve into fashion statements.

Hats have performed a multitude of roles for men throughout time, ranging from simply blocking out the sun to acting as sigils of status.

What about today? How can the right hat serve the right man?


If you’re setting foot into the daunting realm of men’s hats, then you need to know the basics. Gentlemen, that’s why I’ve put this guide together.

Enter the ultimate guide to men’s hats, RMRS-style

  1. Hat Type 1: The Fedora
  2. Hat Type 2: The Trilby
  3. Hat Type 3: The Panama
  4. Hat Type 4: The Porkpie
  5. Hat Type 5: The Boater
  6. Hat Type 6: The Akubra
  7. Hat Type 7: The Flat Cap
  8. Hat Type 8: Baseball Caps

Overview – What is a Hat?

Before we get down to brass tacks, we need a foundation. So, how do we define a hat?

Hats are outlined by the Merriam-Webster dictionary with two definitions:

  • A covering for the head usually having a shaped crown and brim.
  • A distinctive head covering worn as a symbol of office.

The definition gives us two themes: pragmatism and status. It’s not surprising, therefore, that there is such a hybrid approach to the construction of most hats.

Brimmed hats have a few features in common:

hat anatomy infographic
This infographic showcases the different parts of a standard brimmed hat.
  • The crown comprises the top part of the hat. It’s the region that actually sits on your head. The “tip” is its highest point.
  • The pinch refers for any indentations on the crown.
  • Bands are usually strips that are decorative in nature, going around the crown and resting on the brim.
  • A brim, of course, is the hat’s edge. This often protrudes off the sides of the hat and the lower part of the crown. In baseball or flat caps, this is called a bill.
  • Some hats come with interior lining, which comes in various soft fabrics.
  • The sweatband lines the interior of the crown’s base. it helps guarantee a good fit keeps the shape.

Brief General History

Men’s hats have a long history. The first brimmed hat is widely believed to be the Ancient Greek Petasos. It was developed in Thessaly, a region in Greece hailed for its formidable horsemen. The Petasos was often made with felt or straw.

Its utility found itself entering warfare, with the Boeotian helmet sporting a similar brim to offer protection against both the enemy and the sun.

Fast-forward a few thousand years, and we have a dizzying array of brimmed hats which range from the wide fedoras seen in The Godfather to the baseball caps sported by cheesy middle-aged dads all over the globe.

Don’t worry, we’ll get to them all…

1. The Fedora

streetwear trendy look guy

Few men’s hats are as iconic as the fedora. It epitomizes the classic man. It didn’t start that way, though…

The fedora started as a woman’s hat in 1882. It came simultaneously into fame as a play by the same name wherein the main character – a woman named Fedora –  wore the hat.

Though it was an iconic women’s fashion piece for years, that all changed in 1924 when Prince Edward of Britain took a liking to them. At that point, it became a men’s hat. The fedora usurped other forms of headwear.

The fedora is made traditionally of felt. Its crown features an indentation along the top and on each side of the frontal region. It is circled by a band and has a height of approximately 4.5 inches. The brim boasts a minimum width of 2.5 inches but can be much larger.

fedora hat for men
The fedora is a classic staple of menswear.

Should You Wear It?

When it comes to men’s hats, the fedora is synonymous with classic style. If you’re the kind of guy who loves sport coats and blazers, then this may be a winner.

It works best if you keep your look as classic as possible. This means suits, dress shirts, slacks, dress shoes, etc. This is the paragon hat for the classically-minded man.

2. The Trilby

Retro hat man

This men’s hat is often confused with a fedora due to the similarity in appearance, but it’s not the same.

Just like the fedora, however, it has its roots in the theatre in 1894. George du Maurier’s novel, titled Trilby, was eventually adapted into a live performance that featured the hat.

Over time, it was swiftly adopted by the British aristocracy. It was henceforth made popular among horse racing circles. In England, a trip to the racecourse wouldn’t be complete without a tweed suit and a brown felt trilby.

The main difference between a trilby and a fedora is the width of the brim, which is often an inch or less.

trilby men's hat
Though the trilby has some negative connotations as a modern trend, slim men can still pull it off.

Should You Wear It?

These days, the trilby has somewhat of a controversial rep. It is often associated in tandem with the slovenly “neckbearded” man.

What’s more, this men’s hat is also not functional. While the fedora shields your eyes from the sun, the trilby’s shortened brim offers no such protection. It’s more of an aesthetic piece.

Should you wear them? That depends. If you have a medium frame or more, you’d be suited best with a fedora. The brim will only accentuate your width. This hat better compliments the look of a petite man.

3. The Panama Hat

Though it also resembles a fedora, one key feature sets it apart: Straw.

During the 1500s and in the midst of the Spanish conquests, the conquistadors began noticing the elegant headwear sported by the natives of Ecuador. The hats were woven with straw. However, they were so well made that the Spaniards believed the material to be vampire skin.

The name “Panama Hat” is actually a misnomer derived by travelers to South America. Their first encounters with the straw hat occurred in Panama before they arrived in Ecuador.

This men’s hat is traditionally made using straw from the toquilla plant, found only in the rainforests of Ecuador. The general rule of thumb for Panama hats is this: the finer the fibers are and the closer they are in color, the higher quality the hat is.

Should You Wear It?

If you want to make a great statement in the Summer or – better yet – you live in a perpetually hot climate, then the answer is yes.

As a men’s hat, the Panama not only keeps the sun out but keeps your head from getting too hot underneath. The perforated nature of the weave keeps air passing back and forth.

If you are wondering “should I shave my balding head?” but are worried about sunburn then this will be your saving grace.

The Panama melds style and functionality into one powerful tool.

4. The Porkpie

man wearing porkpie hat

This hat made its debut in the 1830s as a women’s hat, but it was adopted by men at the turn of the century.

It got its name through its appearance. The crown has a circular pinch lining a flat top, which likens to a British meat pie. It also showcases a brim that is angled upwards at the edges.

The Porkpie was a hit with Buster Keaton, a silent film actor who was said to own thousands of them. It was also popular with college students in the 30s. Though it largely fell out of use in the 50s, it’s still a viable accouterment to any man.

Most recently, it’s the signature accessory of Walter White, the star character of AMC’s Breaking Bad.

Should You Wear It?

Since the Porkpie can be made of numerous materials, including felt and straw. If you fall in love with this style, you can acquire a collection to use in all seasons and a myriad of outfits.

It’s classic, versatile, and stylish.

5. The Boater Hat

man wearing boater hat

Though its history goes back as early as the 1860s, the Boater wasn’t worn by men until the 1880s. From then on, it became the formal staple for classic summer wear.

These men’s hats experienced a golden era in the very early 20th century, where they were used by men in all manner of summer activities.

It became closely associated with the FBI through agent Melvin Purvis, the man responsible for tracking bank robbers such as John Dillinger and Baby Face Nelson.

As its summer use implies, it’s made with a straw called sennit. The Boater has a slightly oval and flattened crown and either a solid or striped ribbon that goes around it. The brim, like the top of the crown, is flat.

Should You Wear it?

The Boater is somewhat of a novelty these days, its heyday long since gone. It may teeter on being antiquated, but it is still a perfectly acceptable hat to wear in the summer. In fact, its rarity can even send a stronger message than a Panama hat can.

 6. The Akubra

man wearing akubra hat

The word “Akubra” is allegedly derived from the Aboriginal word for “head covering.” It was birthed in Australia by Dunkerly Hat Mills Ltd, established in 1911. Their famous hat was dubbed “Akubra” on August 7th, 1912.

It’s considered by some to be a cousin of the fedora. It resembles one in many ways; the felt construction, the pinches, the overall shape of the crown and brim. However, the Akubra is a much larger hat, the brim’s width being about 3 inches in width.

Should You Wear It?

Though over 100 sub-styles of the Akubra exist, they are designed with the rugged outdoorsmen in mind.

If you happen to be a stylish man who also enjoys trekking the outdoors – be it hiking, horse riding, fishing, or braving the Australian outback, then the Akubra is a strong candidate.

7. The Flat Cap

Man in turtleneck

As a men’s hat, the flat cap is quite old. It was first used in 1571 following an effort by the English government to empower the wool trade. A law was even passed by parliament which made it mandatory to wear it on Sundays.

Since the law was only imposed on the working class, the flat became an intrinsic aspect of middle-class style, even when the law was abolished 30 years later.

By the 1920s, it was beloved by rich and poor alike – especially in the British isles, where the Scots still refer to it as a bunnet. After JFK made it fashionable not to wear hats outdoors, however, it fell out of style.

The flat cap is traditionally made of  – you guessed it – wool, though it often includes tweed and cotton. It’s rounded in appearance with a soft, bloated crown. Peaking out from under the crown is a short bill. The hat is adorned with a cloth-covered button on the top.

Another variant exists with a more voluminous silhouette and 8 panels. The crown is pushed further over the bill. This variant is known by many names such as the Newsboy, Gatsby, Ivy, and Cabbie.

It’s also the signature look of the Peaky Blinders, who are portrayed in the hit BBC show.

Should You Wear It?

The flat cap is becoming more common these days, and it’s a great time to wear it.

Want to know when to wear it? Think of a baseball cap. The flat cap can be worn in the same contexts and serves as an upgrade to any outfit.

Slap it on as a finishing touch, and give your outfit the extra edge that it needs.

8. The Baseball Cap

Out of all the men’s hats we’ve listed, none are so commonly used and abused like the baseball cap. Born from the 1860s and made from straw, it was first used by the Brooklyn Excelsiors, establishing itself as the hat of the sport.

By the 1940s, latex rubber was applied to the inside of the cap to give it more structure. At that point, it more closely resembled the hat we know today. Did you know that it wasn’t even socially acceptable to wear a baseball cap outside of the field until the 1970s?

The hat features a rounded, structured crown often with a button on the very top. Toward the front, there is an elongated bill.

The baseball cap is suitable only for casual situations.

Several sub-styles of the cap have emerged over the years. The trucker hat originated from the 1980s as a promotional giveaway item from farm supply companies. It sports a single foam frontal panel, the rest of the crown perforated. This style is beloved by superstars like Lionel Messi.

The dad cap holts six panels around the crown, and is said to be named after the baseball cap’s sudden popularity among dads in the 90s.

Finally, the flat-brimmed cap, or the snapback, is the trendiest of the lot. This one is used often by the younger crowd, and the flat bill is meant to convey a sense of newness.

Should You Wear it?

The baseball cap is the most casual hat on our list. True to its athletic routes, it is only meant to be worn in the most laid back of scenarios. Do not take this into the office or a job interview, but enjoy it at the family barbeque.

In Summary – Men’s Hats


  1. Hat Type 1: The Fedora
  2. Hat Type 2: The Trilby
  3. Hat Type 3: The Panama
  4. Hat Type 4: The Porkpie
  5. Hat Type 5: The Boater
  6. Hat Type 6: The Akubra
  7. Hat Type 7: The Flat Cap
  8. Hat Type 8: Baseball Caps

As you can see, gents, the possibilities out there. Much like watches, hats can be a practical and stylish extension to your personality. You just need to pick your favorite.

Click Below To Watch The Video – The Ultimate Guide To Hats For Men (How To Find The Right Hat)

FAQs: Guide To Hats For Men

Is there a hat I can wear for both summer and winter?

A classic wool flat cap can transition between seasons. Just choose a lighter weave for summer and a thicker one for winter.

How do I know what hat size to buy?

Measure the circumference of your head where the hat will rest, usually just above the ears and eyebrows, and compare it to the hat sizing chart.

What’s the rule for wearing hats indoors?

Traditional etiquette suggests removing your hat when indoors, especially in someone’s home, at a restaurant, or in public buildings.

How do I pick a hat that suits my face shape?

As a general rule, the shape of your hat should contrast with your face shape. For instance, if you have a round face, a hat with a more angular shape, like a fedora, can complement well.

How should a hat fit on my head?

A hat should fit comfortably—snug but not too tight. You should be able to fit a finger between the band and your forehead.

Can hats cause hair loss?

No, wearing a hat doesn’t cause hair loss. The myth likely arose from hats being worn frequently by men who were already experiencing balding.

Is it okay to customize my hat with pins or patches?

Absolutely! Personalizing your hat can add character and make it uniquely yours.

How do I clean my hats?

It depends on the material. Most cotton hats can be hand-washed, while wool or felt may require professional cleaning.

What hat should I wear for a formal event?

A classic choice is a fedora or a trilby. For more formal occasions like weddings, a top hat could also be appropriate.

What’s the difference between a Panama hat and a fedora?

Panama hats are traditionally made from toquilla straw and have a wider brim, whereas fedoras can be made of various materials and usually have a narrower brim.

Should my hat match the color of my shoes or belt?

It’s not a hard and fast rule, but coordinating your hat with your shoes or belt can pull an outfit together nicely.

How do I store my hats properly?

Store them in a cool, dry place on a hat rack or in a hat box to maintain their shape and avoid dust.

Is it acceptable to wear a sports team cap with a suit?

It’s typically a fashion mismatch. Sports caps are best saved for casual attire or sporting events.

How can I make a statement with my hat?

Choose bold colors, unique materials, or hats with an interesting history, like a beret or a newsboy cap, to stand out in a crowd.


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