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How to Rock a Trilby Hat or Fedora and Look Dope

How to Rock a Trilby or Fedora Hat

After taking a look at the Spring/Summer 2017 runways, it’s safe to say that hats have officially made their comeback.

From Gucci to Tom Ford, the menswear collections all featured fedoras and trilby hats, all styled very differently.

I know, fedoras and trilby hats probably look way too similar for the first glance and it can be a bit confusing, but it’s actually easy to spot out the differences, decide how to style them and which one to pick in the trilby vs fedora war.

Here’s how to look good wearing a Trilby, Fedora or Panama hat.

The Trilby – History and Features

The trilby’s name and history go back to the late 1890’s, and since then, they transformed from an elegant, „rich man” accessory to a more modern and youthful style. When comparing trilby vs fedora hats, make sure to take a look at the brim, crown, and material of the hat. Trilby hats usually have these characteristics.
  • a narrow brim that is angled towards the front, which is the reason why it is usually worn at the back of the head
  • a taller crown it was known as the essential detail for men at horse races and special occasions, trilby hats are made from sturdy materials such as wool and tweed. Since the 2000’s, trilby hats have become retro trend statements and are more often with more casual, modern outfits.

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The Fedora – History and Features

Similarly to trilby hats, fedora hats first appeared in the 1890’s and became statement menswear details in the 1920’s and 30’s. Fedora hats can be easily recognized from….
  • their soft, wider brim
  • an indented crown
The fedora hat kept its popularity throughout the decades and became a popular fashion choice for icons such as Frank Sinatra and Michael Jackson. With their refined design and luxurious materials (such as cashmere, rabbit or beaver felt or wool), fedoras are still representing a specific, edgy and classy fashion style.

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Trilby vs Fedora Styling Guide

After separating the different types, it’s time to ask the regular “how to style it” question. Although styling hats can be generally quite tricky (depending on the occasion, the type of the hat and your personal style), once you know the differences, it is also easier to find the matching clothes for them.


Starting off with the trilby, we’d recommend sticking to a more casual look. Since it has evolved into an edgy accessory, it is the perfect detail for a street style outfit.
  • Wear it with…
    Ripped jeans, simple white T-shirts, denim and leather jackets
These casual clothing items will keep the focus on the hat while giving it a more laid-back vibe. You can also experiment with different color schemes. Either go with a monochrome or all neutral outfits with a pop of color in your hat, or choose a black or grey trilby and match it with burgundy, green or light denim.


With fedoras, you can go in a different direction and pull off a classy look. While trilbies look great with oversized T-shirts and jumpers, keep your fedora look more formal.
  • Wear it with…
    a slim fit blazer, a light blue or white shirt and Oxford shoes
If you are regularly not a fan of the traditional, elegant looks but would still like to wear a fedora, find the balance between casual and formal and choose a denim shirt with black or grey trousers.

Trilby vs Fedora vs. Panama


Besides the trilby and fedora hats, there is also a third style that gained popularity in the past years – the Panama hats. This hat style combines both elegant and very laid back elements effortlessly together.

Panama hats are often known as the “holiday hats” as well, which indicates the best way to style them…keeping it relaxed and fresh with an informal shirt and jeans/pants.



Kentucky Derby Attire

If you’re looking for a hat to complete your Kentucky Derby look, you should go with Fedora, straw Trilby, and a Panama hat. You should also consider some color since generally, Derby hats that men used have solid colors. Pair it with your suit or coat and a pair of brogues, boat shoes or saddle shoes. Don’t forget to wear your derby outfit with confidence and swag.


Here are some outfit inspirations for styling Fedora and Trilby hats


But Most Importantly…

No matter which hat you choose in the trilby vs fedora battle, rock it with confidence.  Wearing a hat, especially for a casual occasion is definitely a bold move. Wearing it with confidence will make you look edgy and comfortable with it, even if you are second-guessing your hat or outfit choice).

Looking for more inspiration?

From styling classic pieces jeans and suits to the craziest new trends, check out more fashion articles, such as our styling guide on olive jackets  here

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