25 Of The Best Men’s Hat Styles: Timeless Investments For Any Sartorial Man (Updates 2022)

Remember when Justin Bieber wore a hot pink beanie to a black tie event? Unless you’re Justin, who can pull off anything (you guessed it, we are Beliebers), a beanie at the Grammys isn’t the most appropriate choice of hat. Then what men’s hat styles are suitable for a black tie event, you ask? We’d go for more formal options like a fedora, flat cap, or even a top hat.

We bet formal attire isn’t the only occasion you need help with. From covering up a bad haircut to sprucing up for a first date, you’ll come to realize you need different hats for various instances. With so many men’s hat styles out there, it’s hard to choose the best one for each scenario, and we sure don’t need another challenge in life.

We’ve put together this extensive list of the types of men’s hats to help you win compliments on your hat anywhere you go—from the beach to the ski resort, we’ve got you covered. Keep reading to discover the vast world of hats and beware that you might end up with a few of these in your cart.

Ah, timeless Americana. Nothing will ever replace the classic baseball hat in this category. Maybe you’re reppin’ your favorite sports team, or perhaps you picked one up as a souvenir on your honeymoon. Either way, everyone has that one go-to baseball hat they wear all the time. And because they’re so essential and often worn for outdoor activities, it’s sad to see them wear out and drenched in sweat so quickly (ew). 

If your good old baseball hat is on the verge of falling apart, now is a great time to find a replacement. For a serious upgrade and a wardrobe refresh, go for something minimal and lowkey like this Signature Cap by Axel Arigato. With subtle details like the tonal “A” embroidery and the universal color, this hat will go well with everything. He’s handsome, and he’ll be your new best friend.

When you think of the colder seasons, a beanie is probably the first thing that comes to your mind. Beanies are the most common go-to for keeping your head and ears cozy, but they can be headache-inducing if they’re too tight. Sure, you can pop an Advil, but the key to cutting out the cause is to invest in a ‘good’ beanie that’s soft, snug, and flexible. 

A classic ribbed knit beanie made with soft, Merino wool like this one by Asket will never go out of style—and yes, headache free. The offering of six timeless colors will make styling a breeze for your winter outfits. But if you ask us, we especially love the burgundy colorway for a homey, holiday feel.

Picture the Peaky Blinders cast. They all wear flat caps just like this Brunello Cucinelli number. Even the brand name makes you want to throw on a three-piece suit and cause some mayhem.

Their virgin Wool Flat Cap is a classic style with meticulous craftsmanship and a comfortable fit. That’s why loyal customers have loved it. You get a little extra pinch of dashing with the flat hat, unlike its baseball counterpart. The familiar brim is still there to provide enough shade, but it’s hidden under luxe fabrics like wool, tweed, and cotton. 

Pair stylishly with casual outfits like jeans and a t-shirt. Or, of course, you can go all-out for the ultimate gentleman’s look with a British checkered suit.

Same Peaky Blinders cast reference, different hat. This one has a button. If the traditional flat cap is like the serious older brother, the newsboy hat is the younger brother that knows how to party. He feels more informal with more volume, added texture and pattern, and a cute button detail.

Whether you’re a fan of the movie series or not, you can’t deny that Kingsman showcases an endless array of jaw-dropping looks. If you’re into the whole British gentleman vibe, this cap is a timeless classic that you’re destined to keep for a lifetime. We especially love the tweed texture (it’s so in right now) and the neutral brown shade that’s super versatile. Pair it with a monochrome cable knit sweater and a dapper wool coat to make you feel and look like a smart gentleman.

Bucket hats were once ‘officially’ known as the fisherman’s hat—for the floppy brim protecting you from sun and rain. But thanks to pop artists like Pharrell Williams, they’re now a statement accessory for fashion enthusiasts. 

As seen on the runways and the fashionistas on the streets of SoHo in New York, bucket hats are the perfect topper to elevate a boring outfit instantly. So why not make it the star of your ensemble by rocking a unique piece like this embroidered one by Corridor? It gives major main character vibes, and we’re here for it.

Al Capone will tell you no mobster movie is complete without a fedora hat in every scene. That’s how rich the history of the fedora became a widely recognized status symbol. And now it’s a wardrobe essential for men—especially the wealthy.

The Italian brand Borsalino has a long-standing history of making tremendous fedora hats since the mid-19th century. We love a good heritage name. The Striped Webbing-Trimmed Wool-Felt Fedora is a gem that stays true to its classy and luxurious identity. It really is the perfect topper for any dressed-up look. Pair it with your blazers or wool coats to pull off an Italian gentleman look.

Meet the summer cousin of the fedora—the straw trilby hat. You can expect to find him chilling at the beach on most days, perhaps sipping on his third margarita. As a cooler version of the classic brimmed hat, trilbys were once viewed as the rich man’s hat as they were often seen at the horse races.

A trilby hat like this one by Paul Smith is ideal with your summer outfits like beachwear or your next BBQ. Whatever the occasion, trilbys are here to keep you cool from the sun. It’s time to embrace your inner Frank Sinatra with this one.

We’ve all been there. After watching Django (or any Western movie, really), you’re hit with a sudden urge to become a cowboy—because they’re that cool. You can’t impulse buy rifles, but you can treat yourself with a cowboy hat to make you feel like a movie star.

Originated from the Mexican Cowboys, they’re meant to protect cattlemen from the hot sun. But thanks to all the glamorized Western movies, the iconic hats now have become a fashion statement.

This Queue Essentials cowboy hat proved its best-seller status with over3,000 positive reviews on Amazon. The cooling straw material and minimal design keep things classy without looking like a Halloween costume.

This cowboy hat will boost up your confidence and earn you compliments on (and off) the ranch. Style it with a fringed leather jacket and western boots for a fun and glam yee-haw moment. Or, if you want to keep things contemporary, top this hat with a white linen shirt and jeans.

Remember when you got a sunglasses tan mark after a sweet nap on the beach? You were made fun of for days (even months)—sun hats are here to protect you from that dilemma. These broad-brimmed hats shade your face, neck, and even shoulders from direct sunlight (and unwanted tans). 

If you’re that guy who’s ready to go camping (or any other outdoorsy activity, really) at the drop of a hat, be sure to keep your sun hat on standby. Stay cool and dry with the bonus of not looking like a tomato at the end of the day with this Bora Bora sun hat by Columbia. It works, but still, don’t forget your SPF.

A dad hat is not your ordinary baseball hat. It consists of a few crucial elements like a comfortable cotton material, a classic six-panel design, and an uncomplicated logo. Whether you’re an actual dad (dog dads count) or not, a dad hat is versatile and practical for your casual outfits—perfect for weekends and vacations. 

Of all the types of men’s hat styles, a dad hat should be in your rotation. Foret Studio’s Raven Cap is the perfect go-to for picnics at the park and weekend brunches. Pair this dad hat with your favorite normcore dad sneakers, Levi’s jeans, and a basic logo t-shirt for an all-out, head-to-toe ‘Dad’ look.

Think of your favorite winter hat. We bet you have a super old beanie you can’t stop wearing even though it’s falling apart, not to mention quite smelly. It keeps you so warm you can’t leave your house without it when winter is at its peak. But you haven’t been able to find a good replacement that’s warm, soft, and comfortable enough to match its excellence. 

Well, here’s one that’ll meet your expectations and give you the utmost coziness you get from your old beanie. Soft as a baby’s bottom, Luca Faloni’s premium cashmere beanie won’t itch your forehead. You’ll want to keep it on all day. It’s best not to fight the urge to get one in every color, plus cashmere gloves and scarves to match. 

These winter hats are perfect with a thick padded jacket and a cable knit sweater. Enjoy your toasty winter.

Get ready to crush summer heat and summer outfits with this Crusher stripe straw hat by Billabong. A summer hat like this will save you from the hot weather troubles. Who hasn’t had a terrible sunburn on their face before? So it’s time your favorite pair of sunglasses gets an inseparable companion to stick with.

The crisp natural shade and cooling straw are like a breath of fresh air on a hot, humid day on the beach. The luxurious vegan suede band adds a nice touch to level up this utilitarian hat into a sophisticated summer staple. At the pool, go topless and wear this hat with your favorite pair of swim trunks for a chill guy vibe. Then, style it with a white linen t-shirt and wide-leg trousers for a fancy dinner by the beach.

No, bowler hats are not associated with the bowling sport. They’re also known as a derby hat in the US if you prefer to avoid the bowling confusion. Anyway, it’s a hard felt hat with a rounded crown and curled-up brim. This style was originally created by the London hatmakers Thomas and William Bowler—think Charlie Chaplin. Along with its fedora and trilby counterparts, it’s one of the most iconic pieces of British style.

Giving off major vintage vibes, this Belfry bowler hat is 100% wool at %100 affordable price. It’s an easy way to add oomph to your formal wardrobe. The feather will make you feel a bit scandalous, too. Elevate your tuxedo look even further with this classic bowler hat for a memorable (and Instagrammable) party moment.

A cowboy hat and a classic fedora had a baby—let’s welcome the felt hat. Typically made with pressed wool or animal fur, felt hats are super soft and super warm. Enter the Superduper hat, which is the modern take on a felt hat. 

The cowboy-fedora hybrid is suitable for most occasions with a classy style—think Johnny Depp vibes. They’re also super low maintenance, like a casual blazer or your go-to pair of black sneakers. That’s a huge plus for the low-key dudes.

The 100% rabbit felt makes it extra buttery to the touch, while the colorful drawstring band gives off a more playful feel. The label and the brand’s trademark ‘earth piece’ is hand sewn to the brim of each hat, making yours truly one and only.

A hat recommended by the Skin Cancer Foundation? Yes, such a thing exists—meet the brimmed hat by The North Face. If wearing sunscreen on your face is not your thing or if you can’t resist a rafting session with the boys in the summer, a brimmed hat will be your best friend. 

This Class V Brimmer is the perfect type of men hat styles to provide protection from painful sunburns. The large brims provide shade, and the moisture-wicking material makes it ideal for water-based activities. This one is available in multiple colors and fun prints. we’d love to keep one of each for various occasions. ‘Aviator navy fly wheel’ for fishing, ‘Sharp green’ for golf, and ‘Beta blue lichen’ for rafting.

Another baseball hat… or is it? This cap won’t look out of place no matter what sport you play, but it’s particularly ideal for golf. Even Tiger Woods agrees. We love to follow Tiger’s footsteps when it comes to anything golf-related, so it’s always best to go straight to his sponsor. The sportswear giant, Nike.

The Dri-FIT fabric helps keep your head dry during your round—perfect for summer games. We also love how the iconic swoosh and timeless silhouette make this hat so versatile. You’re all set to take it from the green to the streets.

Yes, straw hats are indeed the kind that you typically imagine scarecrows wearing. But whether you’re a hardworking farmer or chilling on the beach, nothing beats a good straw hat for shading purposes. 

Tommy Bahama’s straw hat keeps the rays away with its thoughtful features. The inner sweatband keeps your face from turning into a sweat waterfall, the straw keeps your head cool, and the larger brim blocks out the sun. Tommy is crushin’ it with this one.

Style it with your favorite Hawaiian shirt and swim trunks for your next tropical vacation. Or switch out the trunks for a pair of linen trousers to take this look from the beach to a fancy ocean-side dinner.

You’d think a leather hat would attract heat, especially in black. But this hat by Stetson has a special Coolmax fabric that’s breathable and cooling. It’s shockingly perfect for hot summers and outdoor adventures. 

If you haven’t heard, the head-to-toe leather look is in. style this hat with your favorite motorcycle jacket, leather pants, and leather boots for the ultimate macho glam. If you prefer a safer choice, go for a simple, casual vibe. Pair it with your favorite pair of jeans and a crisp white t-shirt for an effortless, laid-back look.

Are you just counting down the days until your next summer vacation at the beach? This Panama hat is perfect for flaunting while sipping your icy margarita (or pina colada, no shame). Of Ecuadorian origin, a Panama hat is specifically made with cool straw or palm—the summer version of the fedora. 

This option by Vilebrequin just looks like a breath of fresh air, doesn’t it? Whether you live in a hot and humid climate or you’re having a relaxing weekend in the Hamptons, this hat will be your best friend. Because it’s so pristine, we’d keep the outfit nice and crisp with a white linen shirt and your favorite chino shorts. Here comes a spotless summer look.

This hat is a subtle lumberjack flex. A trapper hat is a must for suffering through infamously brutal winters. Or if you enjoy outdoor winter activities in general. Whatever the frigid occasion is, you’ll look great in this hat.

With the thick sherpa lining and water-repellent canvas finish, this trapper hat is designed to keep you warm and dry from the rain and snow. For your next ski trip, style it with a graphic sweatshirt and a bold-colored padded jacket. All eyes will be on you down the slopes.

Get your monocle ready, gents. A top hat is another variation of a brimmed hat characterized by a tall, flat crown and a broad brim (Willy Wonka, much?). They’re not at all comical, though—if done the right way, you’ll be able to avoid magician vibes. Top hats mostly appeared in historical politics, and they were a common accessory for upper-class males. But what about now?

It can be intimidating to pull this one off because they’re fairly uncommon in the modern era. However, top hats can still come in handy for formal occasions like weddings, funerals, and white-tie events. Go all out with this GEMVIE top hat for your next event with a three-piece tuxedo and tails. The key here is to wear it with confidence. Maybe just don’t wear it at the beach, the pool, or the park like the product page suggests… Yikes.

A pork pie hat is named after, you guessed it, a pork pie. This style has been popular since the mid-19th century, but these days, it’s most commonly known as Heisenberg’s iconic hat from Breaking Bad. It features a cylindrical crown, flat top, and a short brim, providing a classy and artistic feel.

Kangol’s LiteFelt Pork Pie hat is 100% Wool LiteFelt, meaning it’s extremely lightweight and water repellent. A practical yet dapper piece for men. Style it with a piece of timeless outerwear like an oversized trench coat or a plaid blazer to keep things classy. You might want to accessorize with a cigar pipe too.

Ever wondered why loads of truckers wear trucker hats? As always, advertising. Trucker hats date back to the 1980s when they were given away to truck drivers by the U.S. feed or farming supply companies. Because they often feature a flamboyantly large logo or a humorous slogan that’s very attention-grabbing (looking at you, Ed Hardy), they were perfect promotional items for companies.

Rhude’s option is the definition of a trucker hat in the contemporary world. The breathable mesh panels, striking embroidered logo, and bold colors work together to achieve a simple, tough guy look. Pair the hat with ripped jeans and a graphic tee to bring out the rebellious side you never knew existed.

If you want to snap out of your old and rusty hats, there is no better alternative than a classic snapback hat. Known as the New Era caps that represent MLB, NFL, and NBA teams, snapbacks are a must-have for sports fans. They’re not all limited to the stadiums, though. They also make frequent appearances in the hip-hop scene as well (think Chance the Rapper). 

Remember in high school when you’d wear your snapback backward or even sideways and thought you were oh-so-cool? Snapback caps can still be cool as an adult if styled the right way. Ditch those basketball jerseys and style this snapback with a kitschy graphic tee and a pair of crisp white sneakers. You can even throw on a statement necklace for some extra hip-hop bling.

A panel hat is the adventurous cousin in the baseball hat family. If you’re into the sporty-chic look, this one’s for you. With the brim and a lower, softer front panel, these hats are a great choice for running or cycling. The shorter shape also makes it flattering on dudes with smaller heads or rounded face shapes.

Reigning Champ’s panel hat features mesh for improved breathability and an elastic back tab for a comfy, snug fit. Thanks to these practical features, panel hats work best with a sporty look. Pair it with a half-zip sweatshirt or windbreaker and oversized sweatpants.

How To Choose Men’s Hat Styles

Style

First, determine which types of men’s hats styles work best with your usual style. If you mostly lounge around in sweatpants and hoodies, go with a casual baseball hat or a beanie. If suits are your thing, a more formal fedora or flat cap might be best. If you’re an experimental fashion enthusiast, why not try a statement piece like a cute bucket hat or a trucker hat?

Season

Many hats are seasonless and trendless, but it’s still good to determine the weather before making a purchase. For colder seasons, go for hats with warmer materials like a beanie, trapper hat, wool flat cap, or a felt hat. For warmer seasons, brimmed hat styles like baseball hats or sun hats will protect you from the sun.

Occasion

Occasions are a top concern when choosing between men’s hat styles. For more formal outings, classier styles like a fedora, trilby, or flat cap are great. And the best option for everyday events would be a baseball cap, bucket hat, or beanie.

Face shape

Men with longer and square face shapes will look best in hats with wide brims like cowboy hats or sun hats (avoid beanies). For rounder faces, go for angular styles like a fedora or trilby. If you have an oval face shape, you’re lucky—most hat styles will look good on you.