13 Types of Hats Every Stylish Man Should Know About in 2021

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by  William Barton | Last Updated: 

Want to break out of your baseball cap rut?

I hear you. 

The world of men’s hats can be murky. And they can be difficult to shop for online. What will look good on you? Which brands deliver high quality? 

In this guide, I’ll not only break down the most stylish types of hats for men, but also offer some recommendations from brands I’ve either personally tried or have been endorsed by reputable sources. 

13 Men’s Hat Styles That Will Elevate Your Wardrobe

Straw Hat

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Kicking off our list is the inimitable straw hat. This style has become increasingly popular over the past few years, and I think it’s going to be a real trend in the near future. 

Why? 

Well, a ton of people went full Mumford & Sons a few years back and got themselves a wide-brimmed felt hat. Go to any folk music festival and you’re looking at a sea of people whose style looks straight out of The Oregon Trail

The problem is: felt hats are warm. Too warm for the summer. 

Enter the straw hat. 

You can find several styles of hats under the straw category, including fedoras, sunhats, and cowboy hats, and while I cover those styles later, the full brim straw hat deserves a mention of its own. 

Casually, a full brim straw hat pairs best with a chore coat, worn in jeans, and boots. They also look sharp paired with a short sleeve button down shirt and chinos. If you want to go full boss mode, pair your light straw hat with a linen suit and watch as crowds part for you. 

I don’t recommend getting a dark colored straw hat—these really work best in their natural light color. For darker hats, felt makes more sense and the texture fits better in a fall/winter wardrobe. 

My Recommendation

Goorin Bros. Alejandro Ignacio
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I’m a fan of anything Goorin Bros., but their Alejandro Ignacio straw hat stands out in particular. The leather strip around the crown lends a classy contrast, and the shape is appropriate for summer weddings or any casual outing. 

Flat Cap

model wearing bomber jacket from style plan by frank and oak

The flat cap is a classic hat, and one that’s pretty universally flattering. Some guys don’t like the style—that’s understandable. But this type of hat is usually the first style dudes opt for beside the baseball cap. 

It could be that this style of hat is still popular in the golf world, but the flat cap style is a solid and safe choice in every fashion situation. 

Try a charcoal or black version for more dressy occasions, or opt for a hawthorne color for cooler fall months. 

My Recommendation

Brixton Hooligan Snap Cap
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The Brixton Hooligan is my favorite flat cap. I don’t wear it too often, as I tend to opt for more bodacious headwear like straw hats and the like, but it’s a staple that just works when few other hats would.

I tend to get the most use out of it in the late fall and winter when it’s lightly drizzling, and I want to layer textures on each other—a good wool cap does the trick in that situation.

Wide Brimmed Wool Hat

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Like the straw hat, wider brims are entering the mainstream more and more as people look to more classic style icons rather than what’s new or edgy. Isn’t that interesting? As we progress through the 2020s, men’s style is still drawing inspiration from the 1920s.

Wide brimmed wool hats are an excellent addition to your cool weather wardrobe if you’re feeling adventurous. They have the added benefit of keeping the sun off your shoulders and keeping your head warm, but if you’re anything like me, style comes first. 

A quick note: many hats of this style fall under the fedora category, including my recommendation below. But I felt this particular style deserves a spot on its own because the wide brim is such a distinctive look, and how you style a wide brim vs a short brim is quite different. 

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You can pair a wide brimmed hat with just a plain t-shirt and jeans, or you can rock a vintage look with a denim jacket and relaxed fit chinos. The wide brim makes this a more casual style, and it’s not recommended for formal occasions like weddings. That said, it definitely makes a basic outfit like a t-shirt and jeans more sharp looking, much like a good pair of boots does. 

My Recommendation

Yellow108 Dylan Fedora
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I’ve heard great things about Yellow108 hats from a few of the big hitters in the men’s fashion space. Their wide brimmed hats are made with 100% Merino wool, which strikes a nice balance between warmth and breathability. The Dylan from Yellow108 has a flat structure on top, which keeps the profile lower and gives it more of a modern style sensibility. 

Baseball Cap

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I couldn’t leave the old faithful off the list—it’s just too classic. 

While there’s a good chance you’re trying to get away from the humble baseball cap, they also occupy a necessary place in every guy’s wardrobe. 

With baseball caps, you can go several ways: crisp and new looking, pick up a beater distressed cap, rep a sports team, or wear something neutral. 

I’m personally a fan of the sports team cap. And I like to get mine crisp and new and let it age like a dirty, sunbeaten wine. 

While too many guys rely solely on the baseball cap for their outings, it’s a fantastic choice for casual Saturday strolls. Even if you don’t want to rep a sports team, these types of hats come in the clutch when your hair is getting a bit too long and you don’t want to style it—just throw on a cap, your favorite jeans, and take off for the day. 

My Recommendation

New Era 59FIFTY Los Angeles Dodgers
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I like to keep my baseball caps classic, and for that, I turn to New Era. Their 59Fifty Collection is pretty basic in the style department, and the quality is exceptional. I specifically recommend the LA Dodgers caps because I’ve watched them since I was four. I mean, I guess you could get a cap from a team near you, too. 

Snapback

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Snapbacks are the more chill version of a baseball cap. You can turn to these in all the same situations you would for your standard cap, but you don’t have to worry about measuring your cranium, which is nice. 

Snapbacks are even more casual than the casual cap, and are excellent choices for hikes, runs, or afternoon barbecues. 

Here’s a good game: it’s called Hat Toss, and snapbacks are the best to play with. You take one hat, and try to throw it at least 10 feet and land it on someone else’s head. When you nail it, it’s epic. You can play for hours.

My Recommendation

For snapbacks, you can opt for another sports team, but I like more variety. I’ve been rocking the Vuori Dunes hat on runs and hikes. It features a cool patch on the front and comes in a few different neutral tones that look appropriate for weekend adventures. 

Check out all the hats Vuori offers while you’re there—they have some really cool vintage baseball caps for those less sports-inclined. 

Cowboy Hat

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You don’t have to be a cowpoke to get yourself a 10-gallon hat. These must-have hats for western workwear enthusiasts might be a little out of your comfort zone, but a wool version makes for an excellent cold weather choice. 

The most distinctive aspect of a cowboy hat is the curved brim at the sides. There are hundreds of variations on the style, but I don’t recommend getting one with the sides pinned up at the crown (i.e. fully bent at the sides). That looks pretty hokey. 

My Recommendation

Stetson Marshall 4X Wool Cowboy Hat
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If you want the best of the best, the classic, the icon, you need a Stetson. Specifically, the Stetson Marshall. There’s no other way around it. Opt for wool over straw for a more stylish look, and stick to neutral colors.

Fedora

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Select your fedora wisely. These hats have a dangerous reputation. On one hand, guys who pull this hat off look incredibly cool. 

But it’s also a style staple for pasty teens who spend hours building the perfect virtual girlfriend. 

fedora dance

And it’s also a style staple for dads who talk about their bowling league too much. 

Here’s a quick diagnostic: do you have tattoos? You can wear a fedora. Are you wearing cargo shorts right now? No fedora for you. 

Technically, a fedora is any circular brimmed hat with two indents at the top, but for our purposes, I’m going to stick to the short brimmed style (anything 2” or under). 

Fedoras come in a huge variety of fabrics and colors, and they’re a solid choice year-round, assuming you get the right color/fabric combo.

Toss on a straw fedora in summer to keep the sun off your head, and pair it with a short sleeve button down shirt. Or when it’s cooler, try a navy felt fedora paired with wool peacoat. 

But whatever you do: don’t pair it with cargo shorts, and don’t tell any “band-camp” stories while wearing it.

My Recommendation

Brixton has been my go-to hat place for years. They have a huge variety of really cool looking hats, and what I like most about them is the lower profile and more modern styling.

The Brixton Gain Fedora is a classic example of a felt fedora (they also have straw variants for summer, too). It features an interesting nylon band around the crown for a more sophisticated look. 

Havana

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I hope you have a cigar ready and tons of cut up limes at hand. The Havana hat is another type of fedora, but there are a few key requirements to make it chill enough to be considered fit to wear while sipping a Cuba Libre. 

The Havana hat should be made with white straw—cream is the maximum amount of color allowed. And the brim shouldn’t have fabric around the edge. As for the band around the crown? Have fun with it: any color goes, but the true bosses wear a black band tied into a bow. 

My Recommendation

Ultrafino Havana Straw Hat
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Quite surprisingly for a budget option, the Ultrafino Genuine Havana is the hat equivalent of a bottle of rum and a tall glass of ice. It’ll stay comfortable for up to eight hours while the internal headband wicks sweat away from your forehead for those hot and humid days.

Greek Fisherman Hat

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If you’re looking for a unique style, the Greek Fisherman hat is an awesome looking cap that works well if you wear slim fit jeans and fitted shirts. 

The crown is usually made with unstructured waxed cotton canvas, so it’s quite lightweight and also offers a decent amount of rain protection. These hats are ideal for spring showers. 

Depending on the hatmaker you shop with, a Greek Fisherman hat, or mariner hat will either have a long front visor brim, or a short one. I personally like a shorter brim, as the longer type reminds me a bit of a duck bill. 

My Recommendation

The Brixton Fiddler cap is my favorite version of the Greek Fisherman’s hat. It comes in a variety of colors—some better suited to spring, others that are at home with the changing leaves of fall. 

Most importantly, the bill is short and stylish, so it pairs well with more slim, modern fashion. 

Beanie

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Every man should own a beanie. I’ll just come out and say it. 

If you want to live that beanie life, it makes sense to invest in a good quality wool piece. On the other end of the spectrum, you can get one of those cheap cotton beanies that are especially good for leaving in the trunk of your car and forgetting in your large jacket coat pockets. 

But every man should own a beanie. 

For our purposes here, I’ll focus on the more stylish type. 

Many guys rely on the beanie as their only form of headwear, and while the beanie is versatile and stylish, it can’t handle all that burden. 

In the cold, cold winter months, sure—wear a beanie every day: it’s the most stylish cold winter hat there is. 

But if you live in a more temperate area (like in the US South) you don’t really need a beanie every January day. 

To me, a stylish beanie has a lot of texture. Search for “ribbed” or “waffle” beanies, and something that fits flat on the top of your head (rather than having that strange beanie-nipple coming off the top—what is that?). Also, just aim for a solid color. Too many stripes or team logos and it loses all style points. 

My Recommendation

Away Without Leave Fisherman Beanie | Huckberry
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The AWOL Fisherman Beanie is my favorite style of beanie. It comes in just a few classic colors, has texture for days, and it fits snug on the head. The biggest danger for a beanie is when there’s too much fabric up top and it makes the top of your head look huge compared to your face. This one avoids that entirely. 

Newsboy

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Newsboy caps are fall and winter mainstays, and a fantastic cap to wear if you’re looking to curate a unique looking outfit around a certain style.

The Newsboy hat became way more popular just a few years ago when the show Peaky Blinders came out. Suddenly it seemed like every dude wanted Cillian Murphy vibes, though I can’t blame them. He’s so dreamy. 

The trademark of the style? An oversized crown and short brim. 

These look their best when made with a heavily textured fabric like wool, and it’s a great opportunity to inject a subtle pattern like houndstooth, or even corduroy. 

My Recommendation

The Brixton Brood is my go to for the Newsboy style cap. Like with the rest of the brand’s offerings, they’ve taken an early 20th century style and slimmed it down to work better in a modern wardrobe. 

True Newsboy caps—the kind actual newsboys wore back when newspapers were a thing—were huge. They’d make you look more like Toad from Mario than anything. So I heartily recommend the slimmed Brood from Brixton. 

Straw Sun Hat

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The straw sun hat has been a mainstay of surfer style since the 1960s, but they’re gaining popularity amongst the “young dads who go to a brewery with their baby strapped to their chest” crowd. 

You know why? Because those massive straw sun hats basically scream I know how to party responsibly.

When it comes to the brim on these bad boys, the bigger the better. Obviously, you’re not going to wear this to anything remotely formal, so have fun with it. You can often find these on the cheap, and they’re the perfect choice for music festivals, beach days, or carrying your baby to a brewery. 

My Recommendation

Vuori Beacons Lifeguard Hat
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I like the Vuori Beacons Lifeguard Hat for a few reasons. First, it’s made with lightly colored straw, which is an absolute must for this style. Do not go with a black straw sun hat. That’s just crazy. 

Second, the brim has a cloth binding around the edge, which stops it from fraying too much. And the cloth underneath the brim is dark charcoal colored, which actually helps keep glare off your eyes (that’s also why you’ll see new baseball caps with black cloth under the brim). Science.

Bucket Hat

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Bucket hats aren’t just popular with grandpas going fishing and 90s era rappers. They’re making a comeback in the street style circuit and beyond. 

These are great for keeping the sun off you, and they’re a lightweight and packable alternative to many of the other hats on this list. The style is still a little on the fringe—meaning you’re playing a delicate balance to make sure the bucket hat fashion works with whatever you have going on. 

Me? I wear slim jeans and fitted t-shirts: I just don’t do well with a bucket hat. 

But if oversized tees are your thing, give a bucket hat a whirl.

My Recommendation

If I were getting a bucket hat, I’d get one of the classic choices from Brixton. They’ve nailed the vintage aesthetic, and I trust the brand’s quality. Check out the Alton, which is packable and comes in a variety of neutral and bold colors. 

What are the Best Men’s Winter Hats?

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When it’s the dead of winter, you don’t want to be messing around with a straw hat. You need something that’s going to keep bad weather and cold wind away from your precious head. 

If you’re in Minnesota or Chicago, or some other outrageously cold place, you may just want a fur trapper hat. You know the one: ear flaps, fur at the fringes. 

It’s not the most stylish, but it’s definitely the most warm. For that type, I’d go with something simple like the Columbia Challenger Trapper.

Columbia Challenger Trapper
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But if you’re looking for a winter hat that’s more appropriate for the office or that looks stylish on a mid-January date, I’d opt for the flat cap, or Newsboy style caps, preferably if you can get them in a patterned wool. 

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Generally, covering your ears is the line between formal and casual. Beanies are a good choice for winter because of their warmth, and you can absolutely wear one on a very casual winter date. 

The biggest issue with beanies is that they absolutely destroy any hairstyle you have going on underneath. 

I’ve found that the flat cap and Newsboy style still give you the chance to take your hat off once you’re inside. You’ll have to fix your hair a bit to get it looking decent again, but that’s a whole lot better than crushing your hairstyle to smithereens with a beanie.  

Let’s Put a Cap On It

Hat’s a wrap. I mean, that’s a wrap. 

If you’re looking for some style inspiration on what to wear with your new favorite hat, check out our nifty outfit tool, The Outfitter.

We’ve put together some of our favorite outfits (a few of which feature hats front and center), and you can build a wardrobe based entirely on your hat collection. 

FAQs

What is the most popular type of hat?

Baseball caps are far and away the most popular style of hat. While I think every guy should own a baseball cap, it’s a huge mistake to miss out on the other types of hats men can wear.

Are bucket hats in style?

Bucket hats are coming back in style for many groups: while they’ve always been popular in streetwear, millennials are embracing the style because of their practicality and vintage aesthetic. At the same time, Gen Z is also picking up on bucket hats to match 90s era style.

Are newsboy hats in style?

Yes, newsboy hats have emerged as an excellent winter hat. They’re unique, stylish, and hit a nice balance between formal and casual. They pair well with both a wool peacoat and a short sleeve buttoned down shirt.

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