There used to be a day when a man wouldn’t leave the house without his hat. It was just something that was always part of his outfit. The style of hat changed throughout the year, but warm or cold, a man would always have his stylish yet practical hat.

Over the last 50 years or so, hats have greatly fallen out of the fashion mainstream. That’s not to say a man will look out of place or out of touch wearing one. Quite the contrary actually. A hat nowadays is a bold statement. A way to say you know how to stand out and be seen. Kind of like wearing a pocket watch or a bow tie.

In order for this to be the case though, you must properly wear the hat. Doing this properly is more about when to wear it, not so much how. Though confidence is always a must. So, in this article, I’ll break down the different types of hats and which outfits are appropriate for them so you always look smooth and bold and out of place when wearing your hat.

Fedora

Fedora

Ah, the fedora. We all know it, and either love it or hate it. It is one of the most timeless hat styles out there. Except they have also been taken over by the cheesy and classless. This has led to it being quite a polarizing hat.

A real fedora is a hat with crease all the way down the middle of the crown of the hat, and a pinch on each side of the front of the hat. The brim is reasonably flexible and able to be bent up or down.

If you are going to wear one, I recommend getting a quality fedora and wearing it in more business or formal situations. Don’t wear it for a night out on the town with jeans and a button down. You’ll look like the person who made the hat so maligned in the first place.

Panama

This hat is actually quite in style right now. It is also rather timeless. A real Panama hat is actually Ecuadorian, and it is made from woven leaves of a palm-like plant. It has a softer straw-like feel to the hat and is very, very durable in all weathers.

Panama Hat

A Panama hat looks mostly like a fedora, with similar creases and pinches, though the brim is usually a little larger and more flexible. If you do get a real, quality woven hat, it can be rather expensive. But there are several different quality knockoff versions.

These hats are definitely summer hats. Or warm weather hats, if you live a climate with no real winters. Because they are always white, they can be worn with lighter colored summer suits or with more semi-casual outfits as well. Panama hats are versatile and classic, don’t shy away from them.

Trilby

The trilby is the smaller cousin of the fedora. It has a shorter crown and smaller brim. Otherwise, it looks about the same. It had its heyday in the 1960s, think Mad Man. But it is not very common these days and is sometimes associated with pick-up artists or nerds. Bruno Mars is someone well known who tried to frequently rock this hat.

Trilby Hat

Due to its reputation, the trilby is best worn in a more casual setting. Wear it with a relaxed nature and don’t take yourself too seriously. If you are truly bold, you can go for a retro, Mad Men style look with this hat. Pressed white shirt and skinny black tie with a tie clip type of look, though most men won’t pull this off completely.

Homburg

One of my favorites and also one of the rarest seen hats on this list. The Homburg has had moments all throughout the 20th century but is currently not common at all. It is also a cousin of the fedora. It has a crease down the middle of the crown, the sides can be pinched or not, but the brim is always turned up.

The homburg is also almost always worn in dressier settings. It can look great with a three-piece suit. It stands out quite a bit, so you must wear it with the confidence of a classic man who isn’t afraid to have a timeless style sense.

Pork Pie

The pork pie hat is the Walter White hat. It is also strongly associated with jazz or blues culture. It has a flat crown with a slightly upturned brim.

Pork Pie Hat

The pork pie has a more playful or hipster tone to it, so it is best worn in more casual settings. Don’t wear it with a suit to work. It will look like you’re trying too hard to stand out.

Bowler

This is the most distinct and niche hat on the list for sure. This is the Charlie Chaplin hat. The bowler, or derby, has a rounded crown, no pinches, and short and upturned brim. It is also quite a stiff hat.

The bowler has working-class origins, but today is definitely seen as either gimmicky or eccentric. If you do feel the need to wear one, I would highly recommend it is with a full three-piece suit and attitude like you know exactly what you’re doing.

Boater

The barbershop quartet hat. The boater is always made of straw, has a flat crown and medium length, flat brim. It also always has some sort of ribbon around the crown. This hat also has a very distinct space in style and can be seen as overly eccentric.

The boater was and still is a formal dress hat for the summer months. So, if you want to wear one, do so in the summer with lighter, more colorful suits. And just remember that it’s a bold look.

Flat Cap or Newsboy

This is commonly pictured as the taxi driver hat or possibly from Peaky Blinders (great show if you haven’t seen it). The flat cap is a rounded cap with a soft crown that sits close to the head and has a very short, stiff brim. The newsboy is similar except it has a more bloated, pillow-like crown and usually has a button on top.

Flat Cap

Both of these can be made of virtually any material. They are kind of like the more dressy, stylish version of a baseball cap. Because of their versatility, you can wear them with almost any outfit. Though I would recommend not using them with formal business attire. I think they look best with a semi-casual look and can look awesome with sweaters.

Beanie

The beanie has gone through quite a change over the last 10 years. It used to be a punk skater statement or a strictly functional piece to keep you warm. Now it is a fashion forward cap seen in many styles and with many outfits.

Beanie

Because of the beanie’s popularity and acceptance and real functionality, you can wear it with almost any ensemble but the most formal. If you do opt to wear it with a suit, make sure you have a nice overcoat to match and that the beanie is fitted. Overly large and droopy beanies look immature. And please don’t be the guy to wear one in August. This is a cold weather cap.

Baseball Cap

Recently, the dad cap style of baseball cap has been making its way into dressier styles. I don’t know why. The dad cap is the floppy baseball cap that is all one color and has a longer brim. Men like to wear it with a suit and loafers with no socks. You know the look. It won’t last.

Baseball caps can also be of the snapback or fitted variety. There is nothing wrong with a baseball cap for a casual walk around with friends or a day out at the park. But that’s where they belong, so keep them there.

Tip of the Cap

Hats are still stylish. While less so than they have been over the last couple of centuries, they still fit perfectly well into business or more casual attire while usually making a statement as well. It’s paramount that you choose the right hat for the right occasion and ensemble though, as a hat out place makes you look ignorant or desperate. Not good. So, use these tips to choose the right hat for you and wear it with confidence.

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