I’ve never been a baseball cap kind of guy.

I’ve bought a bunch, but never got used to wearing them.

I do have this navy Polo Sport “dad hat”, the only cap I’ve worn relatively consistently since I bought it 20ish years ago. But in general, hats like this never fit my aesthetic.

I like the idea of hats, but I wanted something more elevated. As I got older and more willing to experiment, I started wearing fedoras.

I’ve tried on and purchased a number of fedoras the past few years. And while I’m no hat expert, I’ve learned a bit about them.

So in this article, I’ll do my best to show you everything I’ve learned about how to wear a fedora – and that will be important to you, should you want to start wearing fedoras too.

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But before we discuss fedoras, here’s a hat style to avoid

Admittedly, the first ones I bought were terrible: cheaply-made straw-like versions with tacky bands and short, stingy brims. I was still learning and didn’t know any better.

Which leads me to my first point.

Trilby hat - Everything You Need To Know About Fedoras

Trilby by Sterkowski

The stingy brim, the sharp, pinched crown, the permanently up-turned brim at the back paired with the a down-angled brim at the front, usually made from a cheap, stiff straw…

This, my friend, is a trilby. It’s not a fedora.

Cheap versions of the trilby you find in run-of-the-mill stores are not worth your time or money.

On top of that, because of their ill proportions, trilbies look good on absolutely no one. If you’re going to venture into brimmed hat territory, go with a classic fedora; avoid trilbies at all costs.

Anatomy of a fedora

I should note that while there are plenty of brimmed hat styles (from Homburgs and Bowlers to Westerns and Porkpies), in this article I’m talking specifically about one type: the classic fedora.

The kind you see in old 50’s movies or in mafia classics like The Godfather.

In general, a fedora is described as a soft felt hat with a lengthwise crease in the crown, two slight front (or side) pinch creases, a medium/wide brim, and a decorative band at the base of the crown where it meets the brim.

Anatomy of a Fedora - Everything You Need To Know About Fedoras

click to enlarge in new tab

There are three main elements of the fedora: The crown, the brim, and the band.

Crown height, brim width, and band width all vary from hat to hat, so I’ll break down the specifics of each below.

Quick note: Wearing a fedora feels weird at first

If you want to know how to wear a fedora for yourself but you’ve never worn a brimmed hat before, it’s gonna feel weird. You’ll think the brim is too wide, the crown is too tall, the pinch looks weird, etc.

As with anything new, it takes a bit of getting used to. You have to actually wear hats to get used to them. It takes a few wears. And believe me, your tastes will change as you acclimate to the style and start to try others.

Another thing: you may feel inclined to approach this whole brimmed hat topic analytically and ask questions like:

  • “What’s the best crown height for my face shape?”
  • ”What’s the ideal crown-to-brim ratio?”
  • ”I’m 6’ tall, have broad shoulders, and a defined jaw. Should I wear a 3” brim or a 3.25” brim?”

First, relax. Take a breath.

Second, find comfort in the fact that there is no right or wrong. It’s all personal preference. Some hats may look better on you than others. That’s for you to decide. It becomes much easier once you try a bunch of hats on.

Speaking of: when it comes to how things fit, my best advice is to go and try a bunch of stuff on (yep, just repeated myself, on purpose).

No matter if it’s jeans, dress shirts, or hats… you have to try plenty of different models and styles to find one that works for you.

You can read all the suggestions in the world but you won’t know how good something looks until you try on 5 other things that look shitty on you. You can’t develop a personal preference until then, either.

So that’s my advice. Go out and try on some hats before getting all analytical about exact measurements and ratios.

The Crown

Even within the family of fedoras, you can have slightly different shaped crowns. Here’s a good forum thread that shows a number of styles.

I’m partial to a shorter crown with a center dent and a gently pinched front. After trying many different crease styles and crown heights, this combo looks the best on me.

The only way you’ll know what looks good on you, as mentioned above, is to try a few. Throw on fedoras with tall crowns, shorter crowns, deep pinches on the front, pinches on the side, etc…

Men who prefer a more custom experience can purchase a hat with an open crown (fully rounded, no creases or dents) and shape one themselves.

One low-risk option would be to try the open crown Briles fedora from Bailey of Hollywood.

The Squatter and the Fedora, both by Akubra, are other great hats to start with if you want to go that direction.

Keep in mind that an open crown is naturally taller to allow for bashing and shaping. Once you’ve done so, the overall height will be shorter. As a rule of thumb, 5.5” would be the minimum height (give or take, depending on your head) needed to do any shaping without the top of your head popping out the dent.

The Brim

wool felt fedora - Everything You Need To Know About Fedoras

Go with a more substantial brim. I’d say around 2.5” is your sweet spot.

There’s a bit of leeway here; if you’re a thin guy with a narrow face, a shorter brim (say, 2”) may look good on you without dipping down into terrible trilby territory.

If you’re a bigger guy or you have a wider face, a slightly wider brim (3-3.5”) may suit you better.

I personally prefer a brim that’s between 2.5″ – 3″.

It’s all about proportion in relation to your head, face, and shoulders… similar to lapel, tie, and collar widths. At the same time, there’s room for personal preference. But again, you have to try on a few models to see what you like best.

The material

straw fedora - Everything You Need To Know About Fedoras

Fedoras are usually made from wool felt, as well as more exotic rabbit, cashmere, and even beaver felt. Warm weather versions are made from straw.

Straw fedoras can look similar to Panama hats, but Panama hats are specifically handwoven in Ecuador, usually from the toquilla palm.

Design details

hat detail closeups - Everything You Need To Know About Fedoras

Fedoras typically come with a grosgrain band of varying height (usually around 1-1.5”).

Adding any accoutrement—feathers, a cool enamel pin, button, monogram, etc.—is totally up to you. This is where the “personal” in personal style comes in. I keep a few feathers and sometimes I’ll wear them in my hat, other times I won’t.

“Can you pack a fedora?”

You can, if you buy one that was designed to be packable.

I have a straw fedora from Goorin Bros. and two wool felt fedoras from Bailey that are packable. This comes in handy when you want to travel with your hat. You simply roll it up and keep in your jacket pocket or carry-on if you don’t want to wear it on the flight.

Articles of Style did a quick and easy hat folding tutorial that you can find here.

Where to buy your fedora

There are plenty of reputable brands to buy your first (or next) fedora. Expect to pay at least $100 for a basic fedora and $250+ for a really nice one.

While I have a decent, growing collection of fedoras at this point, none of mine are on the high end of the spectrum. I believe my most expensive one retails at $150, and I’ve picked up a few on sale.

Here are a few brands to browse:

If possible, I suggest heading to a store and trying on at least 5 different fedoras.

As always, it’s worth it to spend a bit more on quality. But I understand the desire to not spend too much if you’re still testing out something new in your wardrobe.

Goorin Bros.’ Dean The Butcher is one model I’ve noticed looks great on many guys. I own one of these and it’s definitely a favorite.

The Curtis from Bailey is another great model to start with.

Wrapping Up

Thanks for reading! If you’re on Instagram, follow me there for occasional photos of me wearing a fedora.

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8 Responses

  1. Dan B on

    Sorry Barron, but I have to respectfully disagree. Like trilbys, fedoras do not look good on anyone, unless you have time traveled back to the 1930s. There is too much of a mi’lady vibe going on and most people I have spoken with simply laugh when a person puts a fedora on. It screams “trying too hard”.

    Reply
  2. HIEU on

    The hat debate is based on opinion, only. Everyone has their own opinion.

    I can’t rock a fedora, but I can rock a trilby. It all depends on how it looks on you.

    I think saying that you should never wear a trilby or any other clothing article is a burn immature. I mean, most people out there would say that fedoras are ugly, but you wear them. So whose to say that your opinion on the trilby is correct.

    Reply
    • Barron Cuadro on

      Do you wear the trilby as I’ve shown above? Why would you be able to wear a trilby and not a fedora? If you can wear one, you can wear the other.

      My opinion is correct because this is Effortless Gent, a site I own and run, and everything on here is pretty much my opinion, or the opinion of one of our writers 😉

      Style, in general, is largely based on opinion. And my opinion is that I’ve never seen a trilby worn well, unless by Frank or Don or one of those old school examples… and that’s different, anyway, because the guys I’m thinking of and referring to don’t look like Don and Frank. They look like this:

      https://www.dropbox.com/s/v9zolqggwvt64ox/Screenshot%202018-01-29%2008.14.28.png?dl=0

      Reply
  3. Brian on

    I too was going to give you some guff about trilbies until you pointed out that it’s your site, so your opinion is correct. Fair enough.

    I certainly agree about the cheap ones you find at places like Target. Or even if it is one of quality but you look like the photos you posted… then no, just don’t. Those fellas shouldn’t wear a fedora either.

    But what d’you got against stingy brims?? As a thin guy with even thinner neck, I can only wear a short brim, whether a trilby or stingy brim fedora. I look just comical in a standard brim.

    Reply
    • Barron Cuadro on

      Did you watch the video? I mention in there how Frank was a smaller guy and he had to wear a stingy brim fedora / trilby (he switched it up) and how it made sense for him as a smaller guy because of proportions, narrower shoulders, etc.

      I do think that wearing wider brimmed hats works on anyone, it just might feel weird to you, because you’re not used to it (I mentioned this in the video as well, I believe).

      When it comes down to it, you have to decide what you think looks best on you, personally, despite what I say or what any YouTuber or style blog says 🙂 If we’re all in agreement that cheap brimmed hats are to be avoided, that’s good enough for me.

      Reply

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