Trilby Vs. Fedora – How to Rock Them Both

fedora vs trilby

Headwear is one of the most overlooked aspects of modern-day men’s fashion. Beanies look like the only truly popular piece of headgear worn by men around the world. Everything else, however, seems to be fading into obscurity.

Fortunately, there is a glimmer of light in this sea of obscurity and being forgotten by popular fashion. As we get closer, we realize that these glimmers are actually sparks from the clash of two headwear titans that once ruled the world of men’s fashion; Fedora Vs. Trilby.

Dramatization aside, there was a time when both fedora and trilby were an essential part of every man’s classy casual outfits. They faded into obscurity the last few decades, but this is the perfect time to bring them back. Let’s see what these two hats are, how they differ from one another, and how you can rock them alongside your 21st-century outfits and look like a sleek gentleman.

What Is A Trilby Hat?

Classy man wearing wool sweater along with brown hat.

A trilby is a short-brimmed hat. The brim wraps around the hat and points slightly downwards at the front. The rest of the brim is turned slightly upward. These angles on the brim might sound like a minor factor, but they are the largest reason behind the sophisticated look of this hat.

These trilby hats started their popularity with a stage adaptation of the 1894 novel Trilby by George du Maurier. The hat quickly grew in popularity and went mainstream in a matter of months. The name of this new type of popular hat was attributed to the play it originated from, and the rest is history.

The overall design of trilby hats has remained fairly similar over the decades. But the material it is made from has changed completely. The original material for trilby hats was rabbit felt, and now it is made from stuff like wool, tweed and straw.

What Is a Fedora?

Classy man wearing blue formal blazer over grey high neck

A fedora is a hat with a round brim with slightly raised edges. The top of the hat is pinched at the front. This makes it easier to grab, as well as adds a sense of directionality to it. Just like trilby hats, fedoras also became popular after a stage play of the same name in 1891.

Today, fedoras are adored by both men and women around the world. It is the ultimate accessory for a smart-casual outfit. It also doubles as a sun shield for the wearer’s eyes when worn in a slightly forward position.

Modern fedoras are made from durable felt and cotton as these two materials work in almost every situation. Though, you can find fedoras made from other unique materials like leather.

Main Differences Between the Trilby and Fedora

Trilby and fedoras have been confused for each other for as long as their existence. Some never even learned that these two are completely different hats and not slightly different versions of the same one.

The easiest way to tell them apart is with their brim. Suppose you see a wide, relatively flat brim, then it is a fedora without any doubt. On the other hand, if the brim is angled downwards at the front, and has that signature upwards tilt at the back, then it is definitely a trilby hat.

Another way to differentiate between them is the way they’re worn. Trilby hats are worn towards the back of the head in a sort of neutral position. Fedoras, on the other hand, are worn with their front on top of the forehead so that their brim can shield the eyes from the sunlight.

Lastly, appropriate clothes around the hats are also a dead giveaway if they’re worn correctly. We’ll get into more detail shortly, but the gist of it is that trilby hats are seen as more posh and classy while fedoras are the casual chill-time hats. If you see a man wearing a hat over a business casual outfit, it is most likely a trilby.

With that being said, let’s get started with the styling options.

Ways to Wear A Fedora

Here are the four best ways to elevate your sense of style with a well-matched fedora.

Minimalist Fedora

Man wearing hat over blue navy polo.,

Starting things off is one of the easiest to pull off outfits with a fedora. All you need is a pair of blue jeans, a crew-neck white t-shirt, and a plain black fedora. Wear the fedora slightly tilted backward on your head, and you’re good to go. You can add a splash of personality by wearing a silver chain on top of the shirt, but that is it. Any more and the minimalist nature of this attire will crumble. As for the shoes, a pair of white low-tops is the safest option.

Stylish Music Buff

Fedora and music go together like peanut butter and jelly, so the next outfit on our list takes full advantage of that. For this look, you’ll need a pair of navy blue jeans, gray high-top sneakers, a fresh blue button-up, and a plain black leather vest. Finish the outfit off with a matching plain black fedora. Now pick up your guitar, and you’re ready to be the next big music sensation of this era.

Comfy Polo Look

Next up is an attire that not only looks fantastic it is extremely easy to implement as well. Start with a pair of khaki or light brown plaid pants, and wear a pair of matching velvet loafers underneath. Now top the pants off with a blue polo shirt and a distressed brown leather fedora. This is all you need to become the embodiment of stylish comfort.

Urban Leather

The last fedora outfit is also one of the best-looking ones. The combination of a leather jacket and a fedora is not something you see every day, so this look is also going to turn some heads on the street. Start with black jeans, top them with a white mandarin collar shirt, and a black biker jacket. Choose a pair of black high-top shoes for this ensemble, and finally, wear the khaki felt fedora with confidence. This outfit is two-in-one. You can go to class wearing this, and it will fit right in, and then you can wear the same outfit to a nighttime party and look handsome there as well.

Ways to Wear A Trilby

It’s time to become a gentleman with the trilby. Here’s how to rock it successfully.

With a Peacoat

Classy man wearing brown trench coat over all black outfit.

The trilby has a rich history of being worn by the nobles and gents of the old time. So, what better item of clothing to pair it with than a classic peacoat? However, just because you’re wearing classic clothes does not mean that you have to style them in a classic way as well. An amazing blend of old and the new would be to wear a charcoal peacoat over tight-fit black jeans and a plain black V-neck t-shirt. Top it off with a black trilby and a pair of black aviators. Make sure to wear the hat slightly back so that your hair is showing from the front. As for the footwear, a pair of black leather boots would look immaculate.

Classy Gentleman

Wearing classy clothes in modern style is awesome, but what if you wanted to experience the past with your outfit? Well, you need a khaki woolen overcoat in that case. Pair the overcoat with a light blue button-up and a navy blue woolen sweater. Charcoal trousers are the best choice for pants, and a red tie will add a much-needed splash of lively color into the mix. Top it all off with a gray trilby, and you’re ready to be the most well-dressed man at the next business conference.

Casual Trilby

Not all outfits with a trilby have to be super sophisticated and posh. You can definitely rock it with modern casual outfits with ease. A great example of such an outfit would be a plain dark-gray trilby paired with an indigo cardigan and a white V-neck underneath. Light blue jeans would be the pants of choice, alongside a pair of black leather loafers.

Fedora Vs. Trilby FAQs

These are the most frequently asked questions about fedoras, trilby hats, and anything regarding these two.

Can I wear a trilby hat to the office?

Traditionally, trilby hats were worn by business folks that definitely wore them to their offices. But that was a long time ago. So, make sure to check your workplace’s dress code before making it a part of your office attire.

Do fedoras look good on the beach?

Yes, they do. In fact, an outfit consisting of a colorful fedora paired with an even more colorful Hawaiian shirt, white shorts, and blue flip-flops is one of the most stylish beach outfits out there.

Do trilby hats work well in winter?

Yes, they do. But you have to pair them with the right winter clothes. Overcoats and peacoats are a great safe place to start. Once you’re comfortable with those, you can venture into the world of leather jackets and leather trench coats.

What are the different types of fedora hats?

Fedoras come in a lot of different types. Each of these types has something unique and interesting to offer. The most famous ones are:

  • Straw Fedoras
  • Safari Fedoras
  • Pork Pie Fedoras
  • Wide Brim Fedora
  • Small Brim Fedora

Do fedoras look good on little boys?

Yes, little boys look absolutely adorable in fedoras.

Sassy man wearing navy blue formal suit.

Final Words

Hats have been absent from modern men’s fashion for a long time now. It is about time we brought them back and embraced them fully into our lives. Luckily, the debate of fedoras vs. trilby hats is starting to get popular again. Plus, these hats make an excellent starting off point. Fedoras, in particular, are so easy to style that you can easily integrate them into your existing arsenal of outfits without any issues.

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