Best Hats for Men That Make You Look Like A Badass

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Hats not only can say a lot about your personality, but they are an effective, yet subtle way to demonstrate your own unique sense of style.

But here’s the deal:

Wearing the wrong hat can quickly make you look sloppy while also committing a few fashion mistakes.

In this guide we not only review the best men’s hats in 2020, but we also share with you some expert tips on finding the perfect hat to match your face shape and style.

Furthermore, we also share with you a few trademark features that you should be aware of when making your selection.  Not only will ensure that your hat is made of higher quality and last longer, but it will simply look better as well.

Let’s get started:

Tools of Men Helper

To Help You Decide we have researched and reviewed the best hats for men in 2020. Here’s our top picks:

The Best & Coolest Men’s Hats of 2020 Reviewed

1
Brixton Men’s Snapback Hat

Brixton, a brand founded in 2004 in a garage, has grown to achieve worldwide acclaim for their modern-yet-rugged clothes and hats. Their classic men’s snapback hat embodies everything that they stand for: it’s affordable, straightforward, and it looks great.

The snapback is made from 100% cotton, which means your head will stay cool during the summer months. It’s also a hat that won’t be severely damaged by the rain, as cotton is a fabric that generally wicks moisture away fairly well. This is a great hat at a great price – if you’re a guy looking for something simple and stylish, give this hat a look.

Read hundreds of other reviews here on Amazon.

2
Stetson Skyline 6X Cowboy Hat

Stetson is the gold standard in cowboy hats, and their Skyline 6X hat defines the look of a classic cowboy. Though it’s definitely not cheap, this is a quality hat from a recognizable brand. The hat is constructed from fur felt, part of the reason that it’s expensive, and looks great.

Hats constructed from fur felt do require special care, and if you’re careless with your hats, this might not be the one for you.

Read hundreds of other reviews here.

3
Hampui Hats

The Montaro Limited hats from Hampui are rugged, cowboy-style hats for the modern man. These hats have more of a modern touch than Stetson hats do, so if you’re not a fan of the classic cowboy hat style, Hampui might be a great brand to take a look at. This hat is also relatively expensive, but it’s made with warm wool that’s both breathable and comfortable.

This is a great hat to keep your head warm in the winter and cool in the summer.

Read hundreds of other reviews here.

4
Patagonia Tin Shed Hat

Made from sustainable materials including hemp, recycled polyester, and cotton, Patagonia’s Tin Shed Hat is potentially the best winter hat for men on this list. Convertible earflaps keep your ears toasty even in the coldest of winter temperatures, and an innovative blend of fabric insulates your head.

An added bonus of this hat is that you can flip the earflaps up inside the hat when you don’t need them, making this a versatile hat that can be worn in all sorts of climates and situations.

Read hundreds of other reviews here.

5
Huckberry Explorers Cap

The Huckberry Explorers Cap, made by legendary baseball cap brand Ebbets Field Flannels, is a classic hat that is both comfortable and fashionable. This hat goes well with almost any outfit, and Huckberry emphasizes that they’re a great hat for exploring the outdoors.

The hat is made from a cotton flannel material, making it breathable and comfortable in a variety of situations. It won’t be as warm as a wool hat, but it’s one of the warmest baseball cap hats on this list.

Read hundreds of other reviews here.

6
Seager Wilson Snapback

Seager is a relatively new competitor in the hat market; founded in 2015, the brand was created to preserve the aesthetic and quality of Old West apparel. Their Wilson snapback is a classic design that embodies some of that Old West aesthetic, and it’s a durable cotton hat that works well in almost any situation.

The hat is gritty, rugged, and embodies a modern Old West feel – if you like that style, Seager hats are a great option to look at.

Read hundreds of other reviews here.

7
Pantropic Panama Player

Pantropic’s Panama Player hat is an authentic Panama hat that’s a great addition to your collection for summer months. It’s made from genuine Panama straw and woven in Ecuador. Pantropic added a band under the hat to collect sweat from your forehead and a Grosgrain ribbon headband for an added fashionable touch, making this a stylish and comfortable hat to wear even in the hottest of temperatures. This could very well be the best sun hat for men on this list – there’s so much to love.

This hat comes in four sizes, and the size that’s best for you will depend on your head measurements – be sure to take these before you place an order!

Read hundreds of other reviews here.

8
Hat Club – MLB, NFL, NHL, NBA Hats

Hat Club is a modern brand that manufactures some of the best sports hats on the market. Affordable, durable, and fashionable, these hats are great for the modern sports fan. They make hats featuring MLB, NFL, NHL, and NBA teams, so odds are you’ll be able to find your favorite.

Something interesting to note is that most of the caps from Hat Club feature retro styles designed to invoke nostalgia, so your favorite team’s current logo might not make it on the hat.

Read hundreds of other reviews here.

9
Bailey of Hollywood Billy Braided Trilby

Since 1922, Bailey of Hollywood has been creating hats that symbolize refined fashion; their Billy Braided Trilby hat is no exception to that rule. It’s affordable and comes in a variety of colors, and it’s a great hat to wear during the warmer months of the year.

The hat is made from straw, making it a good, affordable alternative to a genuine Panama hat if that’s a style you’re going for.

Read hundreds of other reviews here.

10
Bailey of Hollywood Tino Litefelt Fedora

Fedoras have received a lot of attention, both positive and negative, within the past decade or so. As we mentioned earlier in the article, guys wearing fedoras with cargo shorts and t-shirts have given the hat style a bad name, but fedoras can truly look amazing if paired with the right outfit.

Remember that fedoras are best suited for more formal outfits; think button-down shirts, chinos, suits, clothing of that variety. This fedora looks great and doesn’t break the bank – plus, it’s made from a very warm wool felt material, which means it’ll keep your head warm during winter months.

Read hundreds of other reviews here.

11
Ebbets Field Flannels – Vintage Baseball Hats

Ebbets is a nostalgic hat shop that specializes in making vintage baseball hats. These hats evoke a classic, retro look, and they’re great for guys who want a break from more modern sports hats. These are some of the best caps for men, particularly in casual applications, and they’re all fairly affordable.

Men who love baseball should find some perfect options within Ebbets’ assortment of baseball caps.

Read hundreds of other reviews here.

12
Kangol Wool 504

The Wool 504 hat from Kangol is an affordable, newsboy-cap style hat made from warm wool felt. It’s a great addition to any man’s wardrobe, and this is a perfect hat for fall and winter.

User reviews online praise the hat for being durable, warm, and stylish. The hat provides a sharp, classy look that you won’t be able to find elsewhere.

Read hundreds of other reviews here.

13
FlexFit Hat

This is a bare-bones, no-frills, very affordable hat that’s great if you’re a guy who’s just looking for something to wear. It’s not extremely stylish nor is it from a well-known brand, but the FlexFit hat doesn’t need to be: it’s just a hat. For some men, just a hat is perfect, and that’s why this is such a great option.

Under $20 is hard to beat for a hat, so if you’re looking for something basic that will work with almost any outfit, the FlexFit hat is a great option. It comes in a variety of colors also, so you can opt for something bright or something low-key, depending on your style.

Read hundreds of other reviews here on Amazon.

9 Tips on Finding the Best Hat for You

1. Style / Personality

Hats have been a quintessential element of a man’s wardrobe for centuries. From old-school hats in the 1800s to the baseball snapbacks that are popular today, hats have always maintained a very important place in history. They’re both a statement of style and a great thing to have around on bad hair days; whatever you’re using your hat for, there are plenty of styles to choose from.

Wearing a hat properly is all about knowing what kind of outfit to pair it with. Let’s take the fedora, for example: it’s a fantastic hat. Unfortunately, many guys decided to wear fedoras with cargo shorts and a t-shirt, which is far from the type of outfit that a fedora looks good with. Due to this, fedoras are somewhat of a controversial hat, but they still look great if you’re wearing one with a suit; or on the casual side of things, perhaps chinos and a button-down shirt. The bottom line here is that all types of hats can look great, you just need to make sure you’re wearing them appropriately.

When we’re talking style, men’s hats come in all different shapes and sizes. The four main categories, however, are the following:

Sports / Streetwear Hats

Streetwear and sports hats are your bread-and-butter hat. This category includes sports team hats, snapbacks, and bucket hats. The majority of hats you see worn are this style, and they’re popular because they’re classic and go with just about any casual outfit. No, your Kansas City Chiefs snapback might not look great with a suit, but it’s a great choice for most day-to-day casual outfits.

Classic / Traditional Hats

Traditional hats have made a resurgence in recent years. Our society tends to be nostalgic and fond of styles from the past, and fedoras and newsboy caps are just a few examples of that fondness. These hats are great but aren’t quite as versatile as casual streetwear hats. Fedoras skew formal, and newsboy hats are generally best with slightly more dressy outfits as well (though you can still pull off newsboy caps with casual outfits).

Western

Cowboy hats have been around for a long time and were made popular by the western novels and movies of the early to mid-1900s. They’re still a popular hat choice today, but not with everyone – it takes a certain kind of guy to wear a cowboy hat. If you can pull it off, though, cowboy hats are the ultimate statement of confidence and swagger.

Beach

Beach hats (think a Panama hat) are a semi-popular style of hat that works well in specific situations. They’re not great for day-to-day wear but paired with a casual button-up and a pair of shorts on a sunny day at the coast, beach hats are tough to beat. They’re a great summer option for men who like the style.

We’ll expand on the different types of hats later on in the article, but those are the four big categories you’ll need to consider before diving into a search.

2. Face Shape

Your face shape determines a lot about what type of hat will work on you. Much like with glasses, the style of your hat should complement your face.

  • Oval: If you’ve got an oval face, you can consider yourself lucky when it comes to hats. Your face doesn’t look bad with any style of hat, and you can pull off pretty much anything.
  • Round: A round face is best paired with a hat that has defined angles, as it will help to contrast with and complement the roundness of your face.
  • Square: Quite the opposite of a round face, a square face should be paired with a hat that has softer curves. This will help to soften the squareness of your face and won’t look awkward.
  • Diamond: If you’ve got a diamond face shape, follow the same rules as if your face were square. Rounded hats are the way to go.
  • Heart: A hat with a medium-sized brim will perfectly balance out a heart shape face – fedoras are a great choice here.
  • Pear: With a pear face shape, hats with a full crown and wide brim will help you balance out your wide jawline.
  • Oblong / Stretch Oval: If you’ve got an oblong face, most hats will suit you, but you want to make sure to avoid hats with a tall crown. You don’t want your face length extended, so avoid taller hats!

3. Hat Fit

Hat fit is generally pretty easy to figure out, and there are three main varieties: fitted, adjustable, and stretch.

Fitted

Fitted hats are not the most common type of hat, but they are certainly a great choice, particularly if you are going with a nice or formal hat. You’ll want your measurements to be taken for that perfect fit!

Here’s a video of the process, so you can see exactly how it goes down.

As you can see in the video, most hat measurements should be between 52 and 64 cm (20.5″ to 25.2″). Some shops and hat companies also include inserts with their fitted hats to help fine-tune small adjustments for a perfect fit.

Adjustable

You won’t be hard-pressed to fit an adjustable hat, as they’re extremely common. Adjustable hats generally come in the form of sport team or trucker caps, and they usually involve either a plastic adjustment or a canvas pull tab to adjust the size of the hat.

These are great because they allow you to customize the fit, but the downside to an adjustable style is that they can sometimes look a little bit too casual – they can also fall apart if adjusted frequently or worn at too tight an adjustment. If you’re a guy who wants a versatile, casual hat, an adjustable hat might be right for you.

Stretchable

A hat with a stretchable fit usually looks similar to a fitted baseball cap but has an elastic stretch band on the inside. These allow the hat to fit a wide variety of head sizes. Stretchable hats are generally sold in sizes like small-medium or medium-large, and they provide a comfortable fit around the head without being too rigid.

4. Fabric

There are plenty of different hat fabrics out there – let’s take a look at some of the most popular:

Acrylic / Polyester / Synthetic / Spandex

Synthetic hats are generally the lowest quality of hats. You’ll find synthetic hat materials in sports team hats and other low-cost hats that are mass-produced. Spandex is commonly found in stretchable hats, as it gives a hat the elasticity to fit a number of head sizes.

Cotton

Cotton is a cool, moisture-wicking, breathable fabric that is found on nicer hats. It’s a great pick for the summer months, as it will allow your head to breathe and stay cool. Newsboy caps, bucket hats, and some casual baseball caps can be sourced from cotton. There are plenty of other hat types that are made from common, but those are some of the most popular.

Fur Felt

Authentic fur felt is a material that’s usually reserved for fancy hats, which mostly cost upwards of 500 dollars. These types of hats rely on furs from rabbit, beaver, and other small animals. They’re not the most durable or affordable, but they look great and they signal class and refinement. They must be cared for with proper cleaners and brushes – we’ll go over this later on in the article.

Panama Hat & Straw Hat

Genuine Panama Hat

A genuine Panama hat, believe it or not, is actually not made in Panama. Rather, Ecuador, Mexico, and Colombia are the three biggest manufacturers of real Panama hats. They are usually not made from straw, but instead from tropical palm plants – that’s one way you can determine the authenticity of a Panama hat.

Straw Hat

Straw hats may be similar in appearance to Panama hats, but there are some slight differences. These hats typically are made from paper straw, wheat, or barley, and many of them are made in the USA (source). If you’re looking for an authentic Panama hat, look for one from Central or South America that’s made from tropical palm plants.

Wool & Wool Blends

Wool hats are an animal-friendly alternative to fur felt, and they provide excellent warmth for the winter months. Wool and wool blends can be found on a variety of fedoras, western hats, and newsboy caps. They generally have a textured surface, and tweed is a very common variety of wool hats.

5. Color

When it comes to hat colors, options are limitless. However, just like with most things fashion, dark colors are the most versatile and will work the best with a wide variety of different outfits. The most popular hat colors with men are black, brown, charcoal, and navy. Some manufacturing methods blend different colors, which can provide a plain weave, twill, or herringbone pattern – different types of weaves will offer different styles and color blends. Determining the best hat color for you will change based on what types of outfits you plan to wear it with.

Panama and straw hats are the one exception to endless color options, and as a rule, they are always light yellow to dark golden. These hats are intended to be worn during the summer and have little use outside of the warmer months.

6. Brand

Almost every apparel brand makes hats, but some are certainly better than others. There are plenty of respected brands in the world of hats, and some long-standing brands have a long lineage of respect and heritage. Our favorite hat brands include the following (we’ve grouped them by category here):

Casual

Casual hat brands that we love include New Era, Nike, ’47, and Flexfit. These are all respected brands in the casual hat market, and each of these brands offers something slightly different. Hats from most of these brands are designed to be worn with a variety of casual outfits, and you can rock these hats with shorts, sweats, and pretty much any other casual clothes you’d like to wear.

Formal / Timeless

If you’re looking for something other than a casual hat, timeless designs always win out. These include fedoras and cowboy hats – these types of hats are generally more of a fashion statement than casual hats, and there are plenty of long-standing brands that offer some excellent options when it comes to formal, timeless hats. Our favorite brands for these types of hats include: Bailey of Hollywood, Bollman Hat Company, Borsalino, Country Gentleman, Kangol, Stetson, Goorin Bros, Jaxon/Village Hat Shop, and Brixton.

All of the brands listed above offer different types and styles of hats, but they’re all time-tested brands that offer some of the most formal and timeless designs available.

7. Season / Weather Intent

The season and weather you’ll be wearing your hats in will define what kind of hat you get. Many high-end hats will offer season recommendations, and some types of high-quality fabric will not perform well in rain, snow, or extreme temperatures, so be sure to check those details before you make a final purchase.

Thicker fabrics, such as wool, offer warmth, so these are hats to consider during the winter. In the summer, cooler hats and thinner materials are ideal, making cotton and synthetic fabrics a great choice. During the summer, it’s also helpful to have a hat that protects both your face and neck from sun exposure.

8. Extras

There are a few other small factors you may want to think about; these might not apply to you, but they’re helpful to consider if you’re thinking about buying a hat.

USA Made

There are plenty of hats made in the United States, which is great if you like supporting local and national businesses. The majority of high-end hats are made in the USA or UK, so it’s always great to check where a hat is made before you buy it.

If you want to buy a Panama-style hat made in the USA, look for straw hats. You won’t be able to find authentic Panama hats made in the USA, so it’s best to stick with straw hats.

Water Resistance

If you live in rainy or snowy regions, choosing a hat with water resistance can be key if you plan on wearing your hat frequently. Water-resistant hats can even be great in the summer, particularly if you live in states where heavy summer thunderstorms are common.

UPF / UVA / UVB Protection

Some hats are made with fabrics that incorporate sun-protecting technology and materials, which can help protect your skin from the sun. Having a hat that shields your face and neck from the sun is already great, but if you can find a hat that also has UVA and UVB protection, that’s a bonus. But, as always, don’t forget to wear sunscreen! It’s important even if you are wearing a hat.

9. Price

Hat pricing varies wildly depending on what type and quality of hat you’re looking for. Basic baseball hats and trucker caps are generally very affordable, while more formal, high-end hats will reach the 500-dollar price point and beyond. If you’re looking for a quick buy, though, there are plenty of options around 20 dollars.

The bottom line when it comes to hat pricing is to spend what you are comfortable spending. There are options at every single price point, so you’ll no doubt be able to find something that works for you. Nobody’s going to inspect your hat materials and brand, so if you decide to go with a lesser-known brand or a lower-quality hat, nobody will be the wiser.

Must-Have Accessories for Your New Hat

These are a couple of our favorite accessories to consider if you’re buying a nice hat; each of these accessories will make life with your new hat much easier.

Hat Rack / Hat Stand

A hat rack is similar to a shoe tree; it helps retain the shape of your hat and can keep it looking great for longer. It also helps to draw moisture from your hat – something that’s great for summertime to help dry your hat out from sweat, but it’s also good to have if you’re wearing your hat in a wet winter climate.

Hat Cleaning Sponge & Brushes

Hat cleaning sponges, brushes, and other cleaning products are not necessary for every hat, and it generally depends on the type of hat you own. For the most part, specialized hat cleaning accessories like sponges and brushes are reserved for felt hats; these are typically fedoras and dress hats, so make sure to invest in these if you have a hat that matches that description.

Hat Cleaner

Hat cleaner is a niche type of cleaner that’s generally reserved for felt hats, and different cleaners are made for different hat colors. We recommend that, if you decide to buy hat cleaner, you make sure it’s from a trusted brand or retailer. You don’t want to drop $500 on a hat to ruin it with a $5 cleaner, so think carefully about your purchase.

Hat Jack

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A hat jack can prevent shrinkage in your hat by stretching it when you’re not using it. It helps your hat to retain its shape, and the wood in the hat jack absorbs moisture. This isn’t necessary if you have a cheap baseball cap, but multi-hundred-dollar fedoras and other fine hats can benefit immensely from a hat jack.

Sunscreen

If you’re wearing a hat, there’s a good chance you’ll be out in sunny weather – so don’t forget sunscreen! Just because your hat may protect some of your face doesn’t mean you’re completely shielded from the sun. It’s particularly important to wear hats with added protection for your neck and shoulders, where a hat may not provide full coverage.  We recommend checking out the men’s sunscreen we recently reviewed.

Sunglasses

cary grant sun

Stylish men’s sunglasses and a hat are one of the most iconic fashion duos of all time. They are a completely optional accessory for hats, but there’s not a more classic summertime look than a hat and a pair of Aviators or Wayfarers.

Men’s Hats: FAQs

Answer:

All types! We’re at a bit of a renaissance period where almost any style of hat is fashionable, so wear whatever you think looks good.

Answer:

A hat used to be an absolutely essential part of a man’s wardrobe; look at any photo from the early 1900s or earlier, and you’ll see that almost every man wore a hat. So, what changed? Most people point to JFK. The American president and international icon famously did not wear a hat, and this sparked many men to ditch hats as part of their daily wardrobe.

Answer:

Think about the occasion you’ll be wearing the hat to and the outfit you’ll be wearing it with! Formal clothes and a fedora, casual clothes and a snapback, you get the idea.

Answer:

Darker, more neutral colors tend to go with a variety of outfits, but bold and bright colors can be a great statement if you can pull it off.

Answer:

Hats are usually removed during solemn ceremonies, such as the national anthem, and many men who go to church choose to remove their hats during church. Removing your hat is generally recognized as a symbol of respect.

Answer:

There are plenty of different brands for different types of hats, so evaluate what type of hat you want and go from there!

All the Different Types of Men’s Hats

1. Army Caps

Army caps require little explanation – it’s all in the name. Army caps are baseball-style hats with army logos or symbolism emblazoned on them. Sometimes, army caps have more of a bucket hat style to them, with a traditional baseball cap bill but a bucket-style top section.

2. Baseball Caps

Baseball caps are the most common type of hat for casual occasions – odds are, you’ve seen thousands of them in your life. They’re great to wear with casual outfits, and many baseball caps have sports team logos or other identifiers on them.

3. Beanies & Pull-Ons

Beanies are softer, fabric caps that pull over your head for added warmth. They offer a completely different stylistic look than a traditional hat.

4. Berets

A beret is a soft-crown hat. This can look like a newsboy hat, but it can also have more fabric for a softer look.

5. Boaters

A boater hat is a semi-formal summer hat, traditionally worn in casual boating settings or on the beach.

6. Bowlers & Derbies

Bowler and derby hats are traditional hats that were commonly worn by men in the early and mid 1900s. They can look stylish if paired with the right outfit in the right situation, so don’t be afraid to wear one of these!

7. Bucket Hats

The bucket hat is, essentially, fabric buckets with a brim that are worn on the head. That description makes them sound a lot less appealing than they actually are – they can look great on a wide variety of people.

8. Fedoras

Fedoras are a formal hat that has been around for more than one hundred years, but still maintains strong levels of popularity with modern men.

9. Gamblers

A gambler hat looks like a mix between a bowler hat and a cowboy hat; they are a masculine, semi-formal hat that won’t go well with all outfits, but they work well in the right situations.

10. Ivy Caps, Flat Caps and Newsboy Caps

Ivy caps and flat caps are a traditional hat style, and they’ve been worn for more than a century. They are rounded with a low profile and a stiff brim.

11. Outback Hats

Outback hats are a style of Western cowboy hat, and they’re popular especially in rural areas of the United States.

12. Pork Pies

Not too different from fedoras, pork pie hats are mid-19th century hats that remain popular today.  Breaking Bad fans will note that this is the type of hat worn by the antagonist, Heisenberg / Walter White.

13. Trilbies

A dapper 1930s hat, the trilby is a classic hat that retains popularity today, especially with men who want a more formal look.

14. Trucker Hat

Shaped like a baseball cap, the trucker hat features a foam front coupled with a nylon mesh back (also known as a netback cap).  This style of the trucker hat became popular in the 1960s (source).

15.  Western Hats

Western hats are a very broad category of cowboy and western-style caps; think of brands like Stetson to get an image of what western hats are.

Our Criteria for Choosing the Best Hats for Men

When searching for the best hats for men in 2020, we considered a wide variety of hats in all budget ranges and styles. In the end, it depends on the intent you have for your hat. If you wear shorts and a t-shirt often and just want something casual, the hat that’s best for you will differ from someone who wears formal clothing and attends formal events. There’s something out there for everyone, and we’re confident that our list above represents a wide array of hats.

 

About The Author

Shawn Burns

Shawn is the founder and senior editor at Tools of Men, the leading style and grooming source trusted by men in 187 countries. He started this site with the goal of teaching men proper grooming habits and sensible style. He is an expert in all things men's grooming related. His work has been mentioned on countless sites including The Wall Street Journal, NBC, AskMen, Vice, WikiHow, and the New York Times.

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