When it comes to divisive men’s fashion accessories, nothing tops the hat. But, we’re not talking about baseball caps—we’re talking about fedoras and other similar wide-brimmed hat styles.
It’s no secret that beardsmen love hats. What are the three symbols most often associated with hipsters? Beards, handlebar mustaches, and yup—you guessed it—fedoras. For the record, we aren’t suggesting that you’re a hipster, we’re just noting that beards and hats quite often show up on the same head—and sometimes it’s a hipster’s head.
Don’t get us wrong, we’re pro hats at Beardbrand—seriously, have you seen Carlos Costa’s hat game? That said, the hat can be a difficult style to pull off, and unfortunately, the hat, particularly the fedora, has developed a bad reputation over the past two decades (more on this later).
With that in mind, our goal in this blog is to give you the full rundown on hat styles and how to wear one without looking like a neckbeard meme.
ANATOMY OF A HAT
Before we get into hat styles, let’s do a quick breakdown of a hat’s anatomy.
The crown is the part of the hat that sits on your head. The height and shape of the crown vary depending on the style.
Dent or bash
The dent is the indent formed on the top of the crown.
Crease or pinch
The crease is the indent that is formed on the front or sides of the crown. The pinch, in combination with the dent, forms a hat’s crown shape.
Most hats have a ribbon or band that circumnavigates the base of the crown. The ribbon is an aesthetic feature that may be the same color as the hat or a different color. The ribbon will often have a bow on one side and can be adorned with a pin, feather, matchstick, playing card, etc.
The brim is the part of the hat that provides protection from the sun and rain. The width of the brim varies depending on the style of the hat. The brim may be stiff or floppy. Some are curved, some are flat.
HAT CROWN SHAPES
These are seven of the most common crown shapes found on men’s hats.
An open crown has no dent or pinch. It’s a rounded crown in its purely natural state. It can be left open, or it can be shaped by the wearer.
A teardrop shape features a round C shape at the back of the crown with a pinch crease in front. It looks like a teardrop when looking directly at the top of the hat.
The diamond is similar to the teardrop but is not rounded at the back of the crown.
A narrow, oblong dent in the crown with a slight pinch crease in the front.
The telescope is similar to the open crown in that it has no crease, but the top of the crown is flattened.
The cattleman features a long, narrow center dent running from front to back on the crown and a pinch on each side of the crown. A cattleman is typically more narrow than the center dent. This is the crown shape that you see on a majority of western cowboy hats.
The gus crown is similar to the cattleman except that the back of the crown is higher, creating a downward slope toward the front. A gus crown is typically paired with a larger brim.
FUR FELT HATS VS STRAW HATS
Fedoras, trilbys, cowboy hats, and porkpie hats can all be purchased in either fur felt or straw. Below is a quick breakdown of the most common materials used by milliners.
Not sure when to wear which? Straw hats are for the summer, or when vacationing somewhere hot, fur felt is for every other time of the year.
Fur felt hats are made from a combination of animal fur felt (typically beaver or rabbit) and wool, or sometimes cashmere. Generally speaking, the higher a hat’s animal fur felt ratio, the higher the quality. This quality is often measured using an “X rating” system, i.e., 10x Beaver, 100x Beaver, etc. We’ll talk more about the rating system below.
Toquilla straw is exceptionally flexible, durable, and long-lasting. Toquilla palm trees are native to Ecuador, and it is the only straw used to make authentic Panama hats.
Shantung is a popular, and comparable alternative to toquilla that is used in the manufacturing of many of today’s straw fedoras and cowboy hats. Shantung is derived from high-performance paper that is rolled into yarn. The shantung is coated, which helps to protect the hat but also gives it a plastic feel.
Toyo is similar to shantung in that it is derived from paper. Still, it is generally less expensive and durable than shantung—though you may see Toyo hats comparable in price to shantung and toquilla.
These days, Milan (pronounced mylan) refers more to a weave style than the type of straw. While hats made from Milan straw can still be found, they are far rarer. Most modern Milans are made from synthetic plastics and hemp. Milan weaving features thick braids that circumvent the hat, creating a ribbed appearance.
Raffia palms are native to coastal Africa. Hats made from raffia typically have more of a traditional straw color compared to the very light toquilla and shantung. Raffia hats usually aren’t woven as tightly, making them more bendable. While there are some higher-end raffia hats, they’re generally more functional over fashionable, and can usually be found for under $60. Raffia straw is more commonly seen in Women’s summer hats—think big, floppy straw hats you would see at the beach—but plenty of men’s options are available. That said, raffia is best left to the beach as a form of sun protection or on Halloween if you’re dressing up as Jason Mraz.
At the bottom of the list is seagrass. Seagrass hats feature a loose weave that allows for breathability, but less structure than you find in the tighter woven hats. Like raffia, seagrass hats are relatively inexpensive and considered more of a functional sun-protection hat.
WHAT A HAT’S X RATING MEANS
The x rating on a fur felt hat refers to the quantity of animal fur in the hat. A higher x rating means there is a higher quantity of animal fur felt in the hat, which generally leads to a softer touch and more expensive price tag.
Currently, Stetson sells fur felt hats on their website that range from 3x to 1000x, though a majority of their hats are 6x.
The x rating system can be misleading for several reasons. For one, this rating system isn’t regulated, and it varies between hat makers. A 6x hat from Stetson may not have the same quantity of animal fur felt as a 6x hat from another hat company. Some milliners don’t even use the x rating system.
Additionally, Stetson’s own x rating system has inflated over time. A 5x used to be the best Stetson you could buy, but as noted above, that number is now up to 1000x.
Stetson also gives their straw hats an x rating based on the quality of the straw and weave.
The main takeaway is that if you are comparing different hat models from the same year and company, the x rating can help give you an idea of the hat’s quality.
Let’s jump into the different styles of hats you’ll find at most hat shops, what to look for, and some suggestions on the best ways to wear them—if at all.
The fedora is a wide-brimmed hat with a snap brim, center dent, and pinched crown. A snap-brim means that the brim can be snapped up or down. Brim widths can vary but are typically between 1.5 and 2.5 inches. A short-brim fedora will be around 1.5” and big-brim, or wide-brim fedoras will be 2.5” or larger.
What to look for in a fedora
Like with boots or dress shoes, you should buy the best quality that is within your budget. Entry-level fedoras from Stetson or similar hatters start at around $150 and ascend from there. As we mentioned above, cheap fedoras generally don’t look good and are part of the reason why fedoras have gotten a bad reputation over the past decade.
Fedora brims have one of three edges—a bound edge, raw edge, or welted edge. The welted edge is when the brim is folded back underneath itself and sewn. This is typically an indication of a lower quality hat. The bound edge has a strip of ribbon that is sewn over the edge of the brim. This is the most traditional edge and is still considered a sign of good quality. The raw brim edge is just cut and left unfinished. This is typically seen on the flat-brimmed fedoras that are popular right now. A bound edge and raw edge are both great options.
How to wear a fedora
We’ve got a preference for wider brim fedoras. The narrower the brim, the closer you get into trilby range, and it's hard to look good in a trilby if you’re not Frank Sinatra.
Fedoras with big, flat brims have more western flair and can look really cool, but these can be more difficult to find if you’re not out west.
Most fedoras will have a brim that is naturally curved up in the front and back. Keep the natural curve and leave the front turned up. Snapping the front down is antiquated and can look like you’re trying a little too hard to be Don Draper (see below) or Humphrey Bogart
Here are seven fedora looks from Carlos Costa to give you some style inspiration:
Fedora with fisherman turtleneck and peacoat
Fedora with leather jacket and printed shirt
Fedora with leather jacket and denim shirt
Fedora with polo shirt
Fedora with striped short-sleeve shirt
Raw edge flat-brimmed fedora with printed shirt
Straw fedora with black button-down shirt
Wearing a fedora does not make you Don Draper (or a better musician)
We have to get this out of the way because if you’re going to wear a fedora, you should know what you’re getting into. For most of the past two decades, the fedora has been widely scrutinized and regarded as one of the worst things men can wear.
For a time, wearing one said (at best), “I’m a quirky artist, and yes, I brought a guitar to this party, and I’m not afraid to bust it out and play Wonderwall,” even though no one asked for that to happen.
At worst, fedora fashion became heavily associated with the internet subculture of neckbeards.
Maybe Justin Timberlake brought the fedora back. Perhaps it was the AMC series Mad Men and its widely loved celebration of the styles of the 1950s and 60s (the series ended five years ago, and we’re still getting invited to Mad Men themed parties).
But, here’s the thing, donning a fedora doesn’t suddenly transform you into Don Draper. No one is looking at a man in a fedora in the 21st century and thinking, “there goes a gentleman.” It’s just not the way we think about hats, or more particularly, men in hats anymore. And let’s be honest, Don Draper isn’t exactly a great guy—an interesting character in a well-written period drama? Absolutely—but we can think of better role models.
We aren’t saying that you should avoid fedoras. We think fedoras can be damn cool and still have a place in contemporary men’s fashion—but dropping one on your dome doesn’t automatically make you a dapper gentleman, and it may cause some people to assume that you are not. In fact, some people may automatically assume you’re a creep, as indicated in this Vice article about the history of the fedora.
It’s worth noting that when people are critical of men wearing fedoras, those men are almost always wearing a trilby. Stick with a high-quality fedora and go for a bigger brim—you’ll be fine.
Speaking of the trilby…
The trilby, also sometimes referred to as a stingy brim, is often mistaken for a fedora, though it is notably different. The trilby has a much smaller brim, less than an inch and a half. The front is often permanently angled down, while the back is tipped up.
The crown shape is similar to the fedora, but with a less prominent pinch or crease in the front. Cheaper trilbys won’t have much of a dash or pinch at all.
Perhaps the only two people to ever make the trilby look good were Frank Sinatra and Dallas Cowboys Head Coach Tom Landry—both from a bygone era.
We’d suggest steering clear of them.
The bowler is similar to the homburg, but with an open crown. It was created as a riding hat that would stay on the head while in the saddle. While most people associate the cowboy hat with the wild west, the bowler was the more widely worn hat during that period.
The bowler remained popular into the early aughts before becoming synonymous with Charlie Chaplin, and they’ve never really shaken their connection with the silent film star.
Leave the bowler for costume parties.
The homburg features a center dent crown shape with no pinch and a short, bound-edge brim that is rolled up on the sides. It has the look of a bowler hat but with a center dent crown.
Winston Churchill notably wore one, and they haven’t been seen much since. The Notorious B.I.G. wore a homburg and made it look damn cool—but, let’s be honest, was anyone really going to tell Biggie anything otherwise?
Churchill and Biggie Smalls had larger than life personalities, so the homburg seems fitting for both of them, even though they wore them in different eras.
We’re starting to see more homburgs pop up in hat shops. It’s definitely a dressier hat and should generally only be paired with a well-tailored suit. That said, Carlos Costa makes a convincing argument that the homburg can be paired with a more casual outfit.
The porkpie hat is the Walter White “Heisenberg” hat in the AMC show Breaking Bad. It has a small telescope crown with a narrow brim that is turned upwards all the way around.
We don’t see too many porkpie hats around, probably because it’s hard to wear one without looking like you’re wearing a Breaking Bad costume.
This Uncle Harry fedora by Goorin Bros. has the feel of a more updated take on the porkpie. The taller crown and broader brim make it a bit more accessible in a modern context.
The boater is a straw hat with a telescope crown, flat brim, and colorful decorative band. Initially worn by rowers, the boater is more synonymous with barbershop quartets and depression-era politicians. Similar to the porkpie, it’s tough to make the boater not look like a prop.
If you want to rock the boater, take a page from Cam Newton’s hat playbook and go all-in on 1920s style—but, then again, we aren’t 100% sure if Cam is even making the boater work. Tread lightly.
The cowboy hat—the quintessential symbol of the American West—features the widest brim of all hat types. The cowboy hat began appearing towards the end of the American Civil War when John B. Stetson created the Boss of the Plains hat. Those initial cowboy hats created by Stetson featured an open crown and flat brim, allowing the wearer to shape them to best suit their needs.
The cowboy hat was and still is essential for ranch workers and wranglers in the American Southwest and Mexico. Throughout the late 19th century, Stetson’s Boss of the Plains hat underwent design changes, including the sharply bent brim shape that allows a wrangler to twirl a lasso without interference from the hat.
Most cowboy hats today feature a cattleman’s crown shape, though they can also be found with an open, teardrop, diamond, telescope, and gus crown.
How to wear a cowboy hat
There’s tremendous variety in cowboy hats with plenty of options for crown shape and size, as well as brim shape and size. Cowboy hats are designed to be big and bold, but you don’t want something so big that it makes you look like an 8-year-old. Try on a bunch before picking one.
Take your head shape into account as well. Go for a narrower crown and have the brim curled up a little more than average if you have a thinner head, keeping a slimmer overall hat shape. Check out Country Singer Sam Outlaw for some inspiration.
If you have a round or square face, go for something with less brim curl. We like how Colter Wall keeps it low and wide here with this gambler style cowboy hat. The shorter telescope crown is a good move for Wall, who has a rounder face than Outlaw.
What to wear with a cowboy hat
The cowboy hat is a bold piece. It’s big, and it’s going to get noticed. A good rule to go by with all western wear (cowboy hats, cowboy boots, pearl snap shirts, bolo ties, etc.) is to keep it to two or three items per outfit. The logic is that too much cowboy starts to look campy—like you just stepped off the set of a John Wayne movie.
That advice still holds true in a lot of ways, but vintage-inspired western wear is more accessible in the 2020s than it has been for a long time. We’re entering a bit of a western wear resurgence, and the “rules” are a little more blurry right now.
Once reserved for country musicians, bull riders, Texas politicians, and Nashville bachelorette parties, the cowboy hat finds itself championed by a younger, more diverse population. From country music upstarts like Orville Peck to rappers like Lil Nas X, the cowboy hat is shaking off the notion that it's only for heterosexual white men.
If you’ve always wanted to try one, now is the time, even if you aren’t a cowboy.
You can keep it casual with jeans, a t-shirt, and boots; you can go full nudie suit and a cowboy hat; you can go 1980’s country disco a la Midland, or you can go 1950s vintage the way Charley Crockett does. Maybe just don’t wear one with shorts? Okay, fine, wear it with shorts—but they have to be jorts, and you have to be all-in on the look.
The takeaway here is that we may be entering a new golden age for cowboy hats, and the time to add one to your wardrobe has never been better.
Your location does play a factor in the decision to wear a cowboy hat. If you are in the northeast (the whole east coast in general) of the United States, you won’t see many cowboy hats. As you move west, they become more commonplace. And if you’re in Wyoming, you might look out of place not wearing one.
That said, don’t let your location be the only thing that stops you from wearing a cowboy hat.
The Western Crossover
If you’re on the fence about the cowboy hat, the western crossover is a good middle-ground between fedora and a full-on 10-gallon hat. Western crossover hats feature more traditional western crowns, like the cattleman or the gus, but with a smaller brim size that falls more in the fedora range.
One of the most legendary western crossovers is the Stetson Open Road. This is the hat that Lyndon B. Johnson wore to add a little western swagger to his presidential image.
Check out how Beardbrand’s Sylvester Louis pairs the Open Road with a matching suit and bolo tie. Mike is wearing one in the header photo but keeps the brim curled up on the sides taking his head shape into account.
Why do they call it a 10-gallon hat?
No one really knows for sure, but most historians believe that it comes from a mispronunciation of the Spanish word “galón,” which means hatband. A 10-galón hat would have had a big enough crown to hold 10 hatbands.
There are plenty of straw hat options out there, but none have as much prestige as the Panama hat.
Panama hats come in a variety of shapes, but what makes a Panama hat unique is that it is woven from toquilla straw in Ecuador. Panama hats are most commonly found in a fedora shape, but just because a fedora is made of straw does not mean it’s a Panama hat. It’s similar to whiskey where all bourbons are whiskey, but not all whiskeys are bourbon.
Other styles of the Panama hat include the Optimo, which is a more traditional Panama hat featuring a rounded open crown shape and downward sloping brim (like the Panama Jack logo); and the Monte Carlo, which has a more western look with its telescope crown and wide brim.
The brim is finished one of two ways—the toquilla is woven in what is called a back weave towards the crown, or the edge can be cut and sewn. Look for a Panama hat with an edge that has a back weave—this is considered higher quality.
What to look for in a Panama hat
For a Panama hat to actually be a Panama, it needs to be woven in Ecuador from toquilla straw. A reputable hatter will be able to properly source a hat to make sure you get something authentic. One of the best places to get a truly authentic Panama hat is at Optimo Hatworks, in the Southeastern Arizona town of Bisbee.
The lightness of the straw and fineness of the weave dictate a hat’s quality. Look for a fine or tight weave and straw that is closer to white, and is uniform in color. A higher number of weaves per square inch is more desirable and will be more expensive.
As we mentioned, Panama hats come in a variety of styles, so try on a bunch to find what works best for you.
What to wear with a Panama hat
Light-colored linen is an excellent option for the warm weather vibe of the Panama hat. A light-colored cotton suit with no tie can work as well. Be careful with pairing a Panama hat with seersucker fabrics as this can come across as campy, or trying too hard.
When to wear a Panama hat
This is a warm weather, summer hat, so unless you live in South Beach, keep it reserved for vacations and scorching days out on the water.
FLAT CAPS AND NEWSBOY CAPS
You’ve seen the flat cap and the floppier newsboy cap on Peaky Blinders. Or maybe you know it as the Kangol hat Samuel Jackson wore in the 1990s. They’re also known as driving caps, golf caps, and the cap your Grandfather likely wore. No matter the name you know them by, they’re back in style and are almost as divisive as the fedora.
We like the floppier newsboy version as it doesn’t create such an extreme downward angle on top of the head.
Opt for a newsboy in grey or brown tweed and keep it reserved for fall and winter.
Here are a few style variations worn by Carlos Costa:
TIPS FOR WEARING A HAT
Go to a hat shop or hatter
Yeah, you can find hats at big box department stores, but these are generally cheaply made low-quality hats. When it comes to fedoras and similar styles, cheap hats look bad—period.
Aside from quality, the other benefit of going to a hat shop is being able to talk to an experienced salesperson that can help you find the right hat for your head shape and style.
If you don’t know your hat size, they can help you find it. Even if you do know your hat size, there’s always a variance in sizing between hatters and styles. A 7 ¼” Stetson fedora might fit you perfectly, but that doesn’t mean a Stetson Open Road in the same size will.
If you can, go with a friend whose opinion you trust. Salespeople are great for answering questions and helping you find what you’re looking for, but they’re still trying to sell you a hat. Having a trusted friend that can give you an honest opinion will make for a better hat buying experience.
Most large cities will have at least one hat shop. If you live in a smaller city or don’t live in a city at all, you may need to delay your hat shopping until you’re visiting somewhere that has a hat shop.
A hat should complement an outfit
A hat, no matter how expensive it was, isn’t going to make a poorly thrown together outfit look stylish. If anything, it’s going to look out of place. A hat's role has changed dramatically since the 1950s when it was something that men wore every day with every piece of clothing they owned.
Instead, a hat should complement an outfit and enhance it.
Find a few style icons
Having a few style icons to emulate is a great way to boost your own personal style. Celebrities and musicians can be a great place to start, but keep in mind that they typically have a little more leeway to do whatever they want stylistically. Instagram is an excellent tool for finding style icons. Once you find someone who has a style you want to emulate, start looking at who they are following.
One other thought here—there are a lot of blogs out there that like to list off things guys should never wear. Hats are almost always on those lists. This is why finding a style icon or two is important because, at the end of the day, you should never take style advice from someone whose style you don’t admire.
Confidence is crucial
If you are feeling self-conscious about the hat you are wearing, people are going to pick up on it. You’ve got to own it 100%. Quality hats are expensive, so if you don’t have an immediate reaction of “yes!” then keep looking. There are a ton of hats out there; don’t settle on one if you aren’t all-in on it.
BUILDING UP THE CONFIDENCE TO WEAR A HAT
We hear guys say all the time that they wished they had the confidence to wear a hat. As we mentioned above, if you’re feeling self-conscious in a hat, people are going to pick up on it. So, how do you build up your confidence?
It varies from person to person, but in our experience, the following tips go a long way.
Don’t just focus on hats, but on your entire style
A hat should complement an outfit, not be the focal point of it. Focus on developing your style from the neck down, and not just above it. Find style icons to get inspiration from and start building your wardrobe. This might mean that hats have to wait. It’s better to have your key wardrobe pieces in place before adding complementary pieces like hats.
Focus on your grooming
For all of us at Beardbrand, developing our own unique styles came second to developing our grooming routines and habits. Taking care of your beard, hair, skin, and body will go a long way in giving you the confidence to experiment with your style.
Experiment, experiment, experiment
Experimenting with your style is crucial in determining what feels right and what doesn’t. Once you have the foundations of your style, start adding little things that push your comfort zone a little at a time. You don’t want to overdo it, but adding one item here and there that you wouldn’t normally wear helps you to begin finding what works without attracting too much attention.
Don’t worry too much about mistakes. Everyone has worn absolutely cringe-worthy things. It happens. We all go through phases that we look back on and go, “wtf was I doing?” It’s all a part of the process.
SOME OF OUR FAVORITE HATTERS
When it comes to the classic American hat, it’s hard not to think of John B. Stetson. For style, quality, and affordability, Stetson is still the benchmark.
Located on South Congress St. in Austin, TX, Maufrais exclusively sells Stetson hats. They carry a wide variety of styles, but you can also purchase an open crown hat and have it shaped to your liking.
Goorin Bros. has shops across the United States, and they carry a wide variety of fur felt and straw hats.
We love these custom hats made in Austin, TX, by Ryan McGrath. Trovador only takes custom orders, so be prepared to spend a little more, but you get a hat that is truly a piece of art.
Located in Bisbee, Arizona, Optimo Hatworks features one of the largest selections of authentic Panama hats that we’ve seen. They also carry rabbit and beaver fur felt hats in a wide variety of styles. Want a custom hat? They’ll measure your head with an authentic 19th-century conformateur.
Want to talk about hats, or need some grooming and style advice? Shoot us a message at [email protected], and we’ll be happy to help you out.
Keep on Growing.
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Beardsmen love hats, so we put together this guide to help you find the best hat styles for you, and a few tips on how to wear them with confidence.
Our top two picks for the best hat styles in the 2020s are fedoras and cowboy hats. Avoid the trilby or stingy brim unless your name is Frank Sinatra.
A few tips for wearing a hat:
- Go to a hat shop or hatter. Trying on a variety of hats is crucial in finding the best fit.
- A hat should complement an outfit, not be the focal point.
- Find a few style icons. Beardbrand’s Carlos Costa is a good place to start for hat inspiration.
- Confidence is crucial. If you are feeling self-conscious about the hat you are wearing, people are going to pick up on it.
- Build your confidence by focusing on your overall style, grooming, and gradually expanding the comfort zones of your look.