7 Best Hats For Bald Guys (And Which Ones To Avoid) (2023)

Choosing the best hats for bald guys depends mainly on the occasion.

I’ve been shaving my head for nearly 20 years and I’ve experimented with the majority of hat styles in that time. I won’t be appearing on a catwalk anytime soon, but even I know not to pair a trucker hat with a suit or wear a trapper hat to the beach.

So here’s a complete guide to the best hats for the discerning bald man, for all occasions. I’ve also included some other key considerations, as not all hats will suit all bald heads.

What to look for in a hat if you’re bald

When choosing a hat as a bald man, remember these key points:

1. Comfort: For bald men, a hat that is too tight or itchy can be particularly uncomfortable as there is no hair to act as a buffer.

2. Material: Bald heads are more prone to sweating, so it’s important to choose a breathable and lightweight material that will keep the head cool and prevent overheating.

3. Style: Bald men may find that certain hat styles complement their head shape better than others. For example, a fedora or a beanie may be more flattering for some bald heads than your standard baseball cap.

4. Face shape: The shape of the bald head can be emphasized by the style of the hat. For example, a bald head with a round shape may look better with a hat that has a more angular brim, while a bald head with a square shape may look better with a hat that has a rounded brim.

5. Color: The color of the hat should complement the skin tone of the bald head. Neutral colors such as black or navy can be worn with most outfits and contrast well with a paler skin tone.

6. Occasion: It probably goes without saying, but all the above advice has to be in keeping with the occasion. Don’t wear a trucker hat to a wedding just because it’s a hot day and they’re breathable!

How to choose a hat for your face shape

Some hats, like the baseball cap, are so versatile that they work with any face shape. If you’re out running or playing ‘ball, don’t overthink this one.

However, if you’re putting an outfit together for most other occasions, there is a right way to go about choosing a hat for your bald head:

• Round face: Choose a hat with a brim and an angular crown. Pair a trilby with a formal outfit to elongate your face and create a more defined jawline. Avoid round or beanie-style hats, as they will only accentuate the roundness of the face.
• Square face: Men with square faces tend to have strong, defined jawlines and foreheads, so choosing a hat that complements these features, like a newsboy cap, is important.
• Long face: Choose a hat with a low crown and a brim, such as a trilby. This will shorten the appearance of the face and create a more proportional look. Avoid hats with a tall crown, as they will only elongate the face.
• Heart-shaped face: Trilbys and newsboy caps will help balance the proportions of a heart-shaped face.
• Oval face: If you have an oval face, you are lucky, as most hat styles will suit your face shape. Choose a hat that reflects your personal style and complements your outfit.

The best winter hats for bald guys

Yes, bald people feel the cold more. That’s just science I’m afraid.

If you’re bald, your head is not only going to be a couple of degrees cooler (hair traps the heat), but you’re also missing a shield from those cold winter winds.

Here is my recommendation for a very acceptable winter hat for bald men:

Trapper hat

A good trapper hat is my favorite thing to wear for a cold day walking in the woods with the dogs. It’s so warm and comfortable that I really don’t care if my kids laugh at the flappy ears.

This winter winner covers your whole head, so nobody is any the wiser about your lack of hair. It even keeps your ears warm, something I haven’t otherwise experienced since my long-haired heyday back in the 90s.

The best summer hats for bald guys

When the sun beats down, tanning a bald head is a tricky business. Avoid  sunburn, heatstroke, and embarrassing skin peeling by simply covering up your dome.

Straw fedora

This is the only fedora I’m going to allow, as you’ll see below!

Great for the beach, but not great for windy days back home. If you’re heading for sunnier climes, a straw fedora goes perfectly with a casual, lightweight shirt.

It will provide plenty of protection from the sun and it’s breathable, so your bald head won’t get too sweaty.

The second you get home, you’ll immediately look ridiculous in a straw fedora. As soon as you return, pack it away until your next vacation, when it will magically become cool again!

The best hats for bald guys with beards

Newsboy cap

The newsboy cap enjoyed a renaissance in the mid-2010s thanks to the popularity of the TV show Peaky Blinders.

Once seen as an old man’s choice, the humble newsboy cap is ideal for bald men thanks to being both smart and on-trend. 

Unlike the show’s lead character Thomas Shelby, who is clean-shaven in the show, a newsboy cap looks great with a beard fading up to a bald head. It will also keep your head warm on cooler days.

If you decide to go for the newsboy cap, make sure the rest of your outfit is also on-point by keeping up with the latest fashion for bald men.

The most stylish hats for formal occasions

Pairing a hat with a suit isn’t for everyone and only the most confident and on-trend bald guys would even attempt it.

Nevertheless, there is a potential winner:

Trilby

Trilbies and fedoras are similar in appearance, but the trilby hasn’t been killed off by internet memes about forever-alone teenagers just yet.

Great when paired with a smart overcoat, the trilby does make a bald head quite obvious as it only covers the scalp from the ears up. For this reason, it’s important to try before you buy and make sure it suits your head shape and hair length. 

A bald head naturally looks smaller because of the lack of hair, especially when your outfit has layers that bulk up your upper body. To keep things in proportion and add some detail to an otherwise plain-looking head area, the more stylish bald man can accessorize with a trilby.

Honestly, I’m not brave enough for this one. The trilby is too similar to the fedora and if you’re mistakenly accused of being a fedora-wearing neckbeard, pointing out that it’s ‘actually’ a trilby isn’t going to change that perception.

What is the difference between a trilby and a fedora?

The fedora has a larger brim than the trilby and a taller crown, but other than that, they’re difficult to even tell apart. Fedoras also typically have a creased crown and are made of sturdier materials, while trilbies have a slightly curved brim and are often made of tweed or felt.

The best casual hats for bald guys

1. Baseball cap

A baseball cap is a classic choice to pair with a more casual outfit. It’s brilliantly versatile, especially if you go for a dark color.

I find that the only downside is that when I wear a baseball cap with a freshly-shaved head, it can irritate my scalp, especially around the temples.

You can moisturize your bald head to help soothe your scalp after a wet shave, but you might end up moisturizing your cap, too.

Another issue with a baseball cap and a freshly-shaved head is that it can make you look ill if you have a pale complexion. They pair much better with a tanned face and some facial hair, to give a healthier appearance.

2. Beanie

A beanie is a great choice for a bald man for most casual occasions. Whether you’re wearing it around the house with an old sweater, or covering up in cold weather, the beanie is a baldie’s best friend.

The best thing about a beanie is that it covers your whole scalp. While you should always be confident to show your bald head to the world, strangers wouldn’t know if you had a full head of luscious hair underneath, or a completely bald dome.

If you need real-world proof of this, nobody knew that Tim Pool was bald until a fellow YouTuber whipped off his trademark beanie in public for a video.

As with the baseball cap, I find that the only time this gets tricky is when I’m freshly shaved. Beanies tend to slide around and start to slip up and off my head. If I’m wearing one in winter, my coat and/or scarf constantly try to push it off as I walk and I have to pull it back in place every so often.

Then after a day or two, my head stubble causes a ‘hook and grip’ effect where I practically need a tow truck to peel off my beanie. This can cause irritation, so be sure to moisturize. 

If you find your beanie gripping your stubble, you might want to check for any fibers that are left behind when you remove it. I’ve walked around for hours before someone has pointed out the black fluff stuck to my head!

3. Trucker hat

Trucker hats can look very cool on a bald head, and are a great choice in summer due to how breathable they are. You wouldn’t reach for one for a wedding, but they’re ideal for a more casual setting.

However, make sure you use sunblock underneath a trucker hat on a hot day. The breathability is created by a mesh top that can lead to a sneaky sunburn, and create unfortunate tan lines.

As covered in our article on bald sportsmen, golfer Stewart Cink has made this mistake on more than one occasion!

The tan lines on Stewart Cink’s head match his hat, I’m dead pic.twitter.com/aYDspxJQfH

— CJ Fogler AKA Perc70 #BlackLivesMatter (@cjzero) August 11, 2018

Hats to avoid if you’re bald

1. Bucket hat

This one might be controversial, as there probably is a place for it but it’s so easy to go wrong with a bucket hat.

While it’s lightweight and will keep the sun off your neck, bucket hats are more associated with hip-hop than bald old men, sadly.

Even if you’re balding in your 20s, it takes a very specific style to pull off this headwear. Certainly, anyone over 30 should think twice before choosing the bucket hat.

2. Fedora

There’s a reason there are countless memes about fedora-wearing ‘white knights’.

In the past, a fedora was a stylish piece of headwear for the discerning gent, looking for an accessory to round off a more formal outfit.

These days they’re associated with neckbeards and the friend-zone.

Let’s just leave the fedora on the shelf, shall we?

3. Pork pie hat

I’m on the fence with this one, so let’s play it safe and leave it in the ‘avoid’ category.

It seems that any bald man in a pork pie hat is destined to be called Heisenberg. Since Breaking Bad gave the accessory to lead character Walter White’s criminal alter-ego, the look will forever be associated with the meth-cooking teacher.

If you have a goatee and you don’t mind being compared with Bryan Cranston’s iconic character, go for your life. The pork pie hat is, in itself, a stylish option for a more formal outfit.

Side note: White has terminal cancer in the show, which doesn’t help the feeling that bald men look slightly unhealthy in certain hats. A strong beard is a good way to help this, as all bald men look better with beards (that’s just science).

Does wearing a hat make you go bald quicker?

Wearing a hat doesn’t make you go bald quicker unless it’s overly tight-fitting and air-tight. In extreme cases where a tight-fitting hat is worn for extended periods, rubs at the follicles and doesn’t allow any breathability, traction alopecia can occur. However, this is very rare.

Traction alopecia occurs when hair loss is caused by something constantly pulling hairs away from the scalp. But don’t worry; for the vast majority of balding men or women with thin hair, wearing a hat won’t make any difference.

For men who are coming to terms with their Male Pattern Baldness or still deciding whether to shave their balding heads, hats are helpful. With a hat, you can hide the hair loss that is causing your self-consciousness until you decide to take action.

Once you make the decision to shave your head, you can keep wearing hats or simply let the world see your baldness. If you regret the decision to shave your head, hats can become your best friends for a few weeks!

The main thing is that you find confidence in how you look and don’t let it define who you are.

FAQs

Summary

I’m pretty comfortable with being a bald man, but I do appreciate a good hat.

We baldies don’t get the opportunity to try out new hairstyles, but hats are a great way to change up your look.

Trilbys are great for more formal occasions, while a baseball cap or trucker hat is perfect for a day in your sweats. For the in-between, smart-casual settings you can try out a newsboy cap. 

Straw fedoras are ideal for a day at the beach, but we’ve consigned the regular fedora to the history books thanks to endless internet memes and their association with lonely white knight types.

Finally, when the weather gets cold you can keep warm with a comfortable trapper hat.

Whether you’re just getting used to your newly-bald head or you’re a veteran who just wants to mix up your image, there are plenty of options to try.

Choose what works for you and enjoy being a hat guy.

In the meantime, check out this post all about how to make bald look good.