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The Art of Wearing Hats: 3 Most Popular Types

February 11, 2016

Trends come and go. One's personal style preferences change with age as well. And hats observe all that, laughing, because they know the world is more likely to see a zombie apocalypse than the end of their popularity.

Image source: http://goo.gl/umuu63

For the first article of our new series, The Art of Wearing Hats, we will examine types you may come across today, according to our stylist Gabrielle.

If everything goes as planned, we'll soon deliver more posts that'll go deeper and cover, for example:

  • The history of hats & their importance as a social status indicator
  • Materials, sizes, choosing the right hat
  • How to wear a hat, when to take it off, etc.

Let's start.



Hats you may come across today

If we were to name all hat styles that actually exist or existed in the past, we wouldn't be doing anything else for the upcoming few weeks. Just try and count the ones that are covered on Wikipedia for yourself :)

So, we reached out to our stylist, Gabrielle, for help. She pointed out 3 types of hats she spots the most these days -- either on the streets or on fashion blogs, Pinterest boards or anywhere else where men's style is being discussed.

Here are Gabrielle's 3 most popular hat types:

  1. Fedora
  2. Trilby
  3. Boater

Ready to know more about them?




“This is the ideal men's hat nowadays,” says Gabrielle. And we must agree. It looks elegant, yet not too formal. And you can wear it with practically anything, as you can see from the following examples:


Image sources: https://goo.gl/XLKUIZ, http://goo.gl/11YmLq & https://goo.gl/f6cdJk

The history of the fedora dates back to 1891, when the term was first used. Since then, it's gone through several waves of popularity, which actually peaked around the 1920s in the US, becoming widely popular among gangsters and even today often evoking the Prohibition era.

Public Enemies' John Dillinger sporting his fedora… and gun. Image source: http://goo.gl/4CtS8A

 Some also say that it was the one and only Indiana Jones who helped keep the fedora spirit alive and, when the first movie came out, popularized it among younger generations. Then, during the first years of the 21st century, hipsters discovered it and actually gave not just the fedora but hats in general the social status they once carried -- wearing a hat was suddenly an indicator of how open-minded, creative and independent you are.

However, you certainly don't need to be a hipster, an Indiana Jones fan or a wannabe gangster to love the fedora. Wear it just because it looks great!




Now, this is where things might get a bit confusing. Why? Because the trilby is also called the gentleman's fedora, having once been considered a rich man's hat.

Image source: http://goo.gl/Diov8P

What's the difference between the two? Take a look at the image below, truly worth more than a thousand words.

Image source: http://goo.gl/m96T8H

They might look almost exactly alike, but that doesn't stop Gabrielle from seeing a big difference between the fedora and the trilby:

“Trilby is just so pubescent, mostly boybands wear it…”

It might have something to do with the origin of the hat: “The hat's name derives from the stage adaptation of George du Maurier's 1894 novel Trilby. A hat of this style was worn in the first London production of the play, and promptly came to be known as "a Trilby hat.”

Of course, there are situations when a trilby is not just a sign of your boyhood. Being Don Draper is one of them. Image source: http://goo.gl/oxniHP




OK, it's still February, but time flies, and summer will be here before you even realize it. If you want to get ready today, the straw boater hat should definitely be on your radar.

Gabrielle shares her professional point of view and describes it simply as “sexy,” which might be another reason for you to get the hat, right? :)

Image source: https://goo.gl/Pi75q6

The boater first became popular in the late 19th century, when (no surprise here) boaters and sailors used to see it as an important part of their outfits.

It has always been a rather formal hat, though, which is why even today you don't see too many people wearing it with shorts and flip-flops -- the fedora is much more suitable in that case.

Have you seen The Great Gatsby? Then you've seen the boater and the outfits it used to go with. Image source: http://goo.gl/qoXCQh

Don't get confused if you see this hat named differently. People call it, among other things: a basher, skimmer, cady, katie, canotier, somer, sennit hat, or in Japan, a can-can hat.



Which one to wear and when?

Let's pretend no other hat types exist, and you're supposed to choose one. Which would you choose? We can help.

  • Choose the fedora if you're looking for a hat you can wear year-round. It looks fine with shorts, jeans, sneakers, flip-flops, casual blazers, shirts, basically everything. And it's much more mature-looking than the trilby.
  • Choose the trilby over the fedora when… well, when you absolutely, positively love it. And, for some reason, can't stand the fedora. If you're choosing just some casual hat and don't care about its type too much, we suggest you leave the trilby to others, as Gabrielle's point (“it's for boybands”) is kind of stuck in our heads.
  • Choose the boater if your fashion goal is to stand out. As you can see from the images above, it can look really great, but you must certainly know what to match it with. It's not as easy as just putting on a fedora and going. However, you can be sure that if you manage to incorporate it into your outfit nicely, the fashion police will make you a shining example to others :)


So, which one will you go for? Share your opinion in the comments!

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