How to Wear a Hat With Short Hair

How to Wear a Hat With Short Hair Guys

If you’ve ever gone from long to short hair, you’re familiar with the challenges that come with the transition.

Wearing a hat with short hair is part of the challenge.

The most difficult challenge of all was learning how to wear a hat with short hair, especially with a new short haircut.

Having short hair has made it difficult for people to wear a hat, but I’ve learned a few tips along the way to make hats look good on people and how to wear them.

Here are my top four suggestions for fellow short-haired persons who are attempting to wear their faded cut with a hat:

1. Knit beanies should be placed correctly

When a guy is wearing a knit beanie with short hair, the most important thing is to make sure that it is positioned correctly.

Instead of pulling it straight down onto your head, you should draw it at an angle toward the back of your head.

Take care of your ears, but don’t allow the cap to encroach on your face. It’s also not all the way on, so the rear of the hat is a little floppy.

2. Let a little bit of your hair show

It should be tucked under your chin and pointed straight up towards the heavens. I look like a Conehead, which is not a good thing.

For those of us with short hair, it might appear like we don’t have any hair at all if the cap completely covers our hairstyle.

3. Wear a variety of hats to see what works best for you.

When transitioning from long to short hair, you may need to reevaluate your own style. It’s no longer necessary to wear baseball caps or cloche hats, for example.

On the other hand, many individuals with short hair like to wear these sorts of caps since they feel comfortable in them, so give a variety of styles a try.

Try on a variety of headwear, including fedoras, and don’t be afraid to experiment.

4. Regardless of how short your hair is, wide-brimmed hats are fine option

In addition to protecting your face from the sun, wide-brimmed floppy hats give a dash of glamor to your daily attire.

When it comes to color, you may wear a black or brown (or even burgundy or forest green) one all year long.

Even while you still need to use sunscreen, this does help protect you from the sun, as well as seem more polished.

Hat which suits short hair guys and how to wear them

The hat with a flat brim (Flat hat)

It’s easy to forget that flat caps were formerly popular among the English nobility, especially those who enjoyed hunting and used tweed in their attire.

As time passed, it started to be worn by wayward boyband members and long-time fans of the style who felt their abilities weren’t quite up to par anymore.

Today, though, everything is different.

Due to appearances in series like Peaky Blinders and the Newsboy, the flat hat has made a comeback from the depths of obscurity to become one of the most strangely rakish accessories available.

How to wear it

In spite of its country-like associations, the flat hat may be worn in a variety of ways, from smart-casual to stylish, and it does so with aplomb.

Think of the baseball cap as a model for proper fit: it shouldn’t be excessively tight or have too much surplus fabric to generate an ugly bunching on top of your head.

You run the danger of creating a mushroom cloud if your cap is too large. Then there was the paper route.

Fedora hat

Of course, the fedora is a hat. In addition to that, it’s a piece of headwear with a storied past.

Though its name derives from the Greek term for “gift from God,” the fedora hat has been in and out of vogue since the late 19th century.

Contrary to its former gangster connotations, the man bun is now more often seen perched on the bonces of raffish artistic types, who prefer to keep it hidden.

Soft felt construction, pinched front, teardrop-shaped crown and broad brim differentiate the fedora from the Stetson and pork pie, respectively.

Check out our post on how to wear a pork pie hat

how to wear a hat with short hair
short beard

How to wear it

A lot of people like the fedora, which is why it’s so popular. If you do it well, you’ll be able to quickly infuse a vintage vibe into your current wardrobe.

The director of content at menswear company Spoke London believes a hat like this “won’t work” with trousers, sneakers, and a hoodie.

Make sure you get one that genuinely fits the way you need it to.

When wearing a fedora  James Bay style, you may need to purchase a slightly smaller size in order to keep it in place on your head.”

Traditional tailoring is an excellent way to stand out from the rest of the suit-clad crowd, or you may go casual with a Cuban collar shirt and fitted pants.

Bucket hat

A bucket hat is a hat with a brim. It was just a matter of time until the fashion industry went crazy about Haçienda headwear again after the resurgence of ’90s style over the last few seasons.

It’s no small triumph that the bucket hat has returned to the fashion elite, given that it wasn’t created with aesthetics in mind.

While originally designed to protect Irish fishermen from rain in the early 1900s, it went on to protect the necks of soldiers in the 1940s and during the Vietnam War.

Since then, it has been a fashion staple, moving from a utilitarian item to a statement piece in the 1960s mod trend.

As hip-hop royalty to Madchester men have donned bucket hats in the decades afterwards, they’ve earned the bucket hat some significant street cred.

How to wear it

The bucket hat is back, but you don’t have to wear a throwback tracksuit to wear one. With all due respect to Liam Gallagher, you don’t even have to wear a parka to get the look.

The bucket hat has grown into a streetwear-inspired statement, so let it do the talking for you. If you don’t plan on attending a festival, wear it with simple, understated pieces (think T-shirts and summer knits) in neutral tones.

Baseball cap

The Excelsiors, a Brooklyn-based baseball club, wore the first baseball caps in 1860, making the hat a cultural touchstone.

It was initially designed to screen the eyes of baseball players from the sun due to its prominent peak and back fastening.

Hip-hop aristocracy and current hypebeasts alike have come to rely on it over the last 150 years, making it an essential element of their ensembles.

High-low clothing has finally found its perfect home here, where it sits at the nexus of leisure and the real world.

How to wear it

In suede, leather, or wool, a luxurious twist on a sporting classic like the curved-peaked cap can be worn with just about everything.

The most fashionable way to wear a baseball hat, however, is to combine it with more formal attire like deconstructed blazers and Oxford shirts in a casual ensemble.

Conversely, streetwear-inspired designs like snapbacks and five-panel hats clash with tucked-in clothing, so wear them with both.

Regardless of what kind of hairstyle you choose, make sure it’s in front of you. And he doesn’t vow to ‘Make America Great Again’.


As you can see, there are plenty of options open to you guys out there on how to wear a hat with short hair.

If you hat style has not been featured, let us know what hat you wear and why its great to wear with short hair.

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