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How to Look Great in a Trilby – Top Tips for Men

By Taylor James


Updated on

A trilby hat is an excellent addition to any man’s wardrobe, and it’s a unique yet attractive accessory that can help any man look stylish and put together. 

However, not everyone knows how to wear one correctly, and wearing one without the know-how risks being problematic, no matter how good the rest of your outfit is.

Man wearing a gray trilby

We’ll break it down in this guide, sharing tips on choosing the right trilby for your style and how to wear it so that you look your best. 

Let’s dive in.

Choosing the Right Trilby Hat

The first step to looking great in a trilby hat is choosing one that suits your style. 

That’s your style, not one you’ve just copied online.

There are plenty of different options out there, so it’s essential to take some time to find one that you love. A good hat complements your height, figure, and body dimensions.

If you’re a big guy, a small, petite hat will look silly, just as a big fitted cap would look silly on a smaller guy.

With trilby hats, proportion matters. The average person will want a mid-sized brim, usually around two inches or more. If in doubt, go larger. 

Then looking for style, a trilby hat (in terms of color, style, design, and aesthetic) compliments the rest of your wardrobe. Also, make sure it’s a hat you feel confident in.

Check out these popular trilby options on Amazon for style ideas.

Wearing Your Trilby Hat for the Best Effect

The key to looking great in a trilby is all about confidence. Wear your hat with pride, and carry yourself with an air of sophistication.

There are a few different ways to style your trilby hat, so experiment until you find a look you love. Remember, trilbies are great for formal and informal, casual occasions. They can pop off regardless of whether you’re wearing a suit, a t-shirt, or jeans.

However, follow the general rules of wearing a trilby hat.

Firstly, trilbies are always worn on the back or middle of the head, never so the brim is over the eyes.

Unlike a hat like a fitted cap, trilbies are seldom worn functionally or for sun protection, but always as an accessory that compliments your outfit. Embrace this, and you’ll see the difference in your look.

Man wearing a trilby and holding a guitar

Best Tips for Wearing a Trilby Hat

Now that you know how to choose and wear a trilby hat, it’s time to share some of our top tips for looking great in one. These little things can make all the difference, so keep them in mind the next time you slip on your trilby.

  • Avoid wearing your hat too low on your head. A trilby should sit just above your eyebrows, giving you a confident and stylish look.
  • Be careful with trilbies. There’s a time and place for these hats, which are considered by many to be out of style. If you feel confident and the trilby boosts your outfit, great. If it doesn’t, or you have doubts, then avoid it. Think of a trilby as a high-risk, high-reward hat.
  • Don’t be afraid to experiment with different styles. Trilby hats come in different colors, materials, and designs, so find one you love and have fun with it. Shop around, see what’s out there, and never settle for any old trilby.
  • There are plenty of choices, and if you’re heading out to an event and want to look and feel your best, it’s well worth taking your time rather than getting to the big day and regretting your choice for the entire event. 

While trilbies are dipping in popularity thanks to the rise of other hat types, sometimes donning a trilby could be a perfect choice. Follow these tips, and you’ll be sure to turn heads the next time you step out in your beloved trilby.

About Taylor James

As Philip Treacy once said, “How a hat makes you feel is what a hat is all about.” And on that note, I hope you enjoy your hats and find the site useful. Learn more about Hat Realm's Editorial Process.