How to Match a Hat with an Outfit – Guide for Men

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Last Updated: August 16, 2023

There was a time in 1920 when it was considered essential for a woman to leave her house with a hat on her head; otherwise, it would be regarded as scandalous. The western women back then, of the upper and middle class, were expected to wear hats in order to keep their heads covered and hidden.

But now, as time’s passing and the fashion industry is being evolved, hats have now become a massive part of fashion. People wearing a nicely matched hat with just the right outfit are now considered stylish.

Different Hats for Different Outfits

Hats come in endless styles, and sometimes it gets pretty hectic for a person to choose the right hat that fits well, looks good, and matches perfectly with clothes. That’s why we have decided to give you a hand with this guide on how to match different kinds of hats with various types of outfits.


The fedora is a kind of hat that has quite a lot of history attached to it. Its roots lie in the word “Gift from God”, which is a Greek word. In earlier times, gangsters used to wear them, but it has become a part of recent fashion.

Although it’s a bit tricky to carry, it looks really cool and adds that charming old-school vibe to the temporary look.

Should your hat match your shirt or pants? If you’ve been asking that question, then the answer is both, ideally. It’s best to wear a fedora in a casual way with a Cuban collar shirt and tailored trousers.


In the ’90s, bucket hats were considered the coolest, but their charm faded with time. Now it’s back in fashion and looks really aesthetically pleasing on people wearing it properly. You don’t have to tie up in a retro tracksuit to wear bucket hats. If you’re going to a festival, pair it up with stripped-back essentials (summer knitwear or a classic tee) in dull and de-saturated colors.


Flat caps are often overlooked. They were once favored in a huge amount by the English gentry. In the ’90s, they sort of became the headgear of old-timers. Today, since everything has changed, the value of flat caps got restored again.

The flat caps are considered the most versatile headgears. First things first, if going for a flat cap, make sure to buy the one that’s not too tight or too loose. Also, make sure that the material of your hat matches the fabric of your coat.


Hats often embrace the personality, only if you’re particular about what and when to wear. The Panama hats are the trickiest ones to carry, but they also look the best and give the most significant reward if worn in the proper manner.

To nail it down when wearing a panama hat is not an easy job. Firstly, you’ll be needing a style that looks the best on your face. Go for a larger brim if you have a round face shape and a smaller brim if you have more diminutive stature. Make sure your attire has that modern edge to it. Make sure to avoid all white tailoring.

You can also wear it while being dressed down by basics for a beach wedding or with a suit worn as separates.