What was the most important piece of men’s wardrobe in the early 20th century? Hats. Unless you didn't have enough financial resources, you wouldn't even consider going outside without a hat.

Until a few years ago, not counting a few occasions and places, you couldn't see anyone wearing those. But now, thanks to some tv shows, movies, and celebrities, they are coming back to the fashion world.

Hats are not only fashion accessories, but they are also practical as they can protect you from the sun and cold. Depending on the hat style you choose, they can also add a touch an eccentricity, nostalgia or fun to your outfit.

But choosing a hat needs careful deliberation, as it can also make you look too eccentric and out of place, as some of them are not meant to be worn to formal or casual places. In this article, I want to introduce you to 8 types of hats for men to hopefully help you choose a good one.

Panama hat

A panama hat is a traditional brimmed straw hat originating from Ecuador. A curious thing is that despite the name, these hats were never produced in Panama.

These hats started booming in popularity in the mid-19th century, during the Gold Rush in California. And in 1906, U.S. President Theodore Roosevelt was photographed wearing a Panama hat. Examples of other men wearing these panama hats include Winston Churchill, JFK, Mick Jagger, Anthony Hopkins, Paul Newman, Benedict Cumberbatch, David Beckham.

The great thing about this hat is that you can match it with almost any casual or formal outfit, adding a certain touch of elegance.

Panama hats vary in styles and should be chosen to suit your face shape. Usually, a larger brim suits large men with round faces, and smaller brim suit men of smaller stature.

Pork pie hat

A pork pie hat is a hat resembling a pork pie, and hence the name.

The pork pie hats were worn primarily by British and American women around 1830-1865, and it only began to appear in US men’s wardrobe in the 1920s, attributed to Buster Keaton, a silent film actor who wore these hats in many of his movies. It is said that he made around a thousand of these hats by converting fedoras and other hats.

While Buster Keaton introduced these hats to the US, its heyday began during the Great Depression, as a few famous men wore during that era, for example, Frank Lloyd Wright, and Lester Young.

Silent for many years, it rose in popularity thanks to the cult series Breaking Bad, as Walter White wore it many scenes as Heisenberg.

Great for casual or smart outfits, you should wear it just like Heisenberg, placing it directly on the top of your head on the sitting level.

If you have a long, short or oval-shaped face, then great, you will be rocking this hat. But if you have either a round or square face, you should probably avoid it.

Fedora hat

Fedora hats have a soft wide brim and indented crown. It was a staple of men's fashion during the early 20th century, worn in almost any public place and occasion. A symbol of wealth and status.

One of the reasons for its popularity is attributed to it being a favorite headwear of Edward, Prince of Wales.

Nowadays, it has become increasingly popular in the fashion world along with a few other classic hats, such as the pork pie and the homburg.

There are many celebrities seen wearing these, for example, Johnny Depp, Justin Timberlake, Brad Pitt, and Michael Jackson. Some tv shows and movies (Mad Men, Shutter Island, Boardwalk Empire) also featured these fedora hats, thus increasing its exposure.

Nostalgic and bold. If you are aiming for this, then you should consider wearing these fedora hats, especially with oxfords and tailored suits.

Trilby hat

A trilby hat is a narrow-brimmed type of hat, viewed in their prime as “rich man’s favored hat”. Though it is very similar in style to fedora hats, and thus are often confused with them, there is a difference. The trilby hats have a smaller brim and taller crown than the fedoras and are worn from spring to autumn at the back of your head.

Due to most people favoring the fedora hats over these trilby hats, they are not particularly popular nowadays, but if you have a smaller face, you should try one, and it may just surprise you.

Homburg hat

A homburg hat, a cousin of the fedoras, popularized in the late 19th century by King Edward VII as a less formal alternative to the top hats.

US President Eisenhower wore a homburg hat instead of a top hat at his first and second inauguration.

Just like other formal Western male headgear, it stopped appearing in the fashion world from the 1960s.

A homburg hat was always considered to be more distinguished and traditional than the fedoras, so it is a perfect hat for businessmen, politicians, and other western gentlemen.

While it is seen more in recent years, it is still not too popular, so you should consider a homburg hat if you want to make a bold statement.

Bowler hat

A bowler hat, also known as Derby in the US, is a hard felt hat with a rounded crown. It is durable and protective. Popular in the UK, Ireland, and the east coast of the US.

It was designed to be a close-fitting, low-crowned hat for the working class, and later in the early 20th century, it began to be associated with the City Gents - businessmen working in the financial district.

The most popular hat in the American West is not the cowboy hat or the sombrero, but the bowler hat, and it makes sense, as it is not easily blown off the top of your head by strong winds while riding a horse, or when sticking your head out of the train.

There are a lot of notable figures wearing this hat, such as Charlie Chaplin, John Cleese, and Curly Howard.

While less traditional than the homburg and fedora hats, it’s still recommended to wear with your formal outfit.

Boater hat

A boater hat, a king of a formal summer hat worn by men, and particularly popular in the late 19th century and the early 20th century. The boater hats were especially popular when boating or sailing, hence the name.

The boater hat is a part of the uniform of the Princeton University Band since 1952, and is a common part of the school uniforms in many boys’ schools, such as Shore School, Brisbane Boys’ College, Harrow School, Knox Grammar School, Wynberg Boys’ High School, Maritzburg College, and many others.

The boater hat, is a formal hat, and it’s an equivalent to the Homburg in the formality, so you should wear it with a blazer, black tie, or a smart lounge suit.

Bucket hat

A bucket hat, featuring wide, and downward-sloping brim, is a hat first adopted as a fashion item in the 1960s with the revival of street fashion. Originally, the bucket hat was introduced around 1900 and was primarily worn by Irish farmers and fishermen to protect themselves from the rain.

Rising in popularity in the late 1980s among rappers as a part of the street fashion, these bucket hats appeared again in the fashion world after being featured by celebrities such as Rihanna.

Conclusion

As you've seen, there are many hat types, and in this article, I wrote only about several classics. To be clear, these hat types still have some variations.

There are some suggestions when choosing a hat by your face shapes, such as the panama hats for diamond face shapes, the boater hats for rectangular face shapes, and the fedora/trilby hats for round face shapes.

While these tips can be helpful, you don't have to stick to them, and choose a hat you like the most. The most important thing when choosing/wearing a hat is to be bold and be confident.