Men's hats – while born out of practical necessity, often evolve into fashion statements.
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Hats have performed a multitude of roles for men throughout time, ranging from simply blocking out the sun to acting as sigils of status.
What about today? How can the right hat serve the right man?
If you're setting foot into the daunting realm of men's hats, then you need to know the basics. Gentlemen, that's why I've put this guide together.
Enter the ultimate guide to men's hats, RMRS-style
Overview
Before we get down to brass tacks, we need a foundation. So, how do we define a hat?
Hats are outlined by the Merriam-Webster dictionary with two definitions:
The definition gives us two themes: pragmatism and status. It's not surprising, therefore, that there is such a hybrid approach to the construction of most hats.
Brimmed hats have a few features in common:
Men's hats have a long history. The first brimmed hat is widely believed to be the Ancient Greek Petasos. It was developed in Thessaly, a region in Greece hailed for its formidable horsemen. The Petasos was often made with felt or straw.
Its utility found itself entering warfare, with the Boeotian helmet sporting a similar brim to offer protection against both the enemy and the sun.
Fast-forward a few thousand years, and we have a dizzying array of brimmed hats which range from the wide fedoras seen in The Godfather to the baseball caps sported by cheesy middle-aged dads all over the globe.
Don't worry, we'll get to them all…
Few men's hats are as iconic as the fedora. It epitomizes the classic man. It didn't start that way, though…
The fedora started as a woman's hat in . It came simultaneously into fame as a play by the same name wherein the main character – a woman named Fedora – wore the hat.
Though it was an iconic women's fashion piece for years, that all changed in when Prince Edward of Britain took a liking to them. At that point, it became a men's hat. The fedora usurped other forms of headwear.
The fedora is made traditionally of felt. Its crown features an indentation along the top and on each side of the frontal region. It is circled by a band and has a height of approximately 4.5 inches. The brim boasts a minimum width of 2.5 inches but can be much larger.
When it comes to men's hats, the fedora is synonymous with classic style. If you're the kind of guy who loves sport coats and blazers, then this may be a winner.
It works best if you keep your look as classic as possible. This means suits, dress shirts, slacks, dress shoes, etc. This is the paragon hat for the classically-minded man.
This men's hat is often confused with a fedora due to the similarity in appearance, but it's not the same.
Just like the fedora, however, it has its roots in the theatre in . George du Maurier’s novel, titled Trilby, was eventually adapted into a live performance that featured the hat.
Over time, it was swiftly adopted by the British aristocracy. It was henceforth made popular among horse racing circles. In England, a trip to the racecourse wouldn't be complete without a tweed suit and a brown felt trilby.
The main difference between a trilby and a fedora is the width of the brim, which is often an inch or less.
These days, the trilby has somewhat of a controversial rep. It is often associated in tandem with the slovenly “neckbearded” man.
What's more, this men's hat is also not functional. While the fedora shields your eyes from the sun, the trilby's shortened brim offers no such protection. It's more of an aesthetic piece.
Should you wear them? That depends. If you have a medium frame or more, you'd be suited best with a fedora. The brim will only accentuate your width. This hat better compliments the look of a petite man.
Though it also resembles a fedora, one key feature sets it apart: Straw.
During the s and in the midst of the Spanish conquests, the conquistadors began noticing the elegant headwear sported by the natives of Ecuador. The hats were woven with straw. However, they were so well made that the Spaniards believed the material to be vampire skin.
The name “Panama Hat” is actually a misnomer derived by travelers to South America. Their first encounters with the straw hat occurred in Panama before they arrived in Ecuador.
This men's hat is traditionally made using straw from the toquilla plant, found only in the rainforests of Ecuador. The general rule of thumb for Panama hats is this: the finer the fibers are and the closer they are in color, the higher quality the hat is.
If you want to make a great statement in the Summer or – better yet – you live in a perpetually hot climate, then the answer is yes.
As a men's hat, the Panama not only keeps the sun out but keeps your head from getting too hot underneath. The perforated nature of the weave keeps air passing back and forth.
If you are wondering “should I shave my balding head?” but are worried about sunburn then this will be your saving grace.
The Panama melds style and functionality into one powerful tool.
This hat made its debut in the s as a women's hat, but it was adopted by men at the turn of the century.
It got its name through its appearance. The crown has a circular pinch lining a flat top, which likens to a British meat pie. It also showcases a brim that is angled upwards at the edges.
The Porkpie was a hit with Buster Keaton, a silent film actor who was said to own thousands of them. It was also popular with college students in the 30s. Though it largely fell out of use in the 50s, it's still a viable accouterment to any man.
Most recently, it's the signature accessory of Walter White, the star character of AMC's Breaking Bad.
Since the Porkpie can be made of numerous materials, including felt and straw. If you fall in love with this style, you can acquire a collection to use in all seasons and a myriad of outfits.
It's classic, versatile, and stylish.
Though its history goes back as early as the s, the Boater wasn't worn by men until the s. From then on, it became the formal staple for classic summer wear.
These men's hats experienced a golden era in the very early 20th century, where they were used by men in all manner of summer activities.
It became closely associated with the FBI through agent Melvin Purvis, the man responsible for tracking bank robbers such as John Dillinger and Baby Face Nelson.
As its summer use implies, it's made with a straw called sennit. The Boater has a slightly oval and flattened crown and either a solid or striped ribbon that goes around it. The brim, like the top of the crown, is flat.
The Boater is somewhat of a novelty these days, its heyday long since gone. It may teeter on being antiquated, but it is still a perfectly acceptable hat to wear in the summer. In fact, its rarity can even send a stronger message than a Panama hat can.
The word “Akubra” is allegedly derived from the Aboriginal word for “head covering.” It was birthed in Australia by Dunkerly Hat Mills Ltd, established in . Their famous hat was dubbed “Akubra” on August 7th, .
It's considered by some to be a cousin of the fedora. It resembles one in many ways; the felt construction, the pinches, the overall shape of the crown and brim. However, the Akubra is a much larger hat, the brim's width being about 3 inches in width.
Though over 100 sub-styles of the Akubra exist, they are designed with the rugged outdoorsmen in mind.
If you happen to be a stylish man who also enjoys trekking the outdoors – be it hiking, horse riding, fishing, or braving the Australian outback, then the Akubra is a strong candidate.
As a men's hat, the flat cap is quite old. It was first used in following an effort by the English government to empower the wool trade. A law was even passed by parliament which made it mandatory to wear it on Sundays.
Since the law was only imposed on the working class, the flat became an intrinsic aspect of middle-class style, even when the law was abolished 30 years later.
By the s, it was beloved by rich and poor alike – especially in the British isles, where the Scots still refer to it as a bunnet. After JFK made it fashionable not to wear hats outdoors, however, it fell out of style.
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The flat cap is traditionally made of – you guessed it – wool, though it often includes tweed and cotton. It's rounded in appearance with a soft, bloated crown. Peaking out from under the crown is a short bill. The hat is adorned with a cloth-covered button on the top.
Another variant exists with a more voluminous silhouette and 8 panels. The crown is pushed further over the bill. This variant is known by many names such as the Newsboy, Gatsby, Ivy, and Cabbie.
It's also the signature look of the Peaky Blinders, who are portrayed in the hit BBC show.
The flat cap is becoming more common these days, and it's a great time to wear it.
Want to know when to wear it? Think of a baseball cap. The flat cap can be worn in the same contexts and serves as an upgrade to any outfit.
Slap it on as a finishing touch, and give your outfit the extra edge that it needs.
Out of all the men's hats we've listed, none are so commonly used and abused like the baseball cap. Born from the s and made from straw, it was first used by the Brooklyn Excelsiors, establishing itself as the hat of the sport.
By the s, latex rubber was applied to the inside of the cap to give it more structure. At that point, it more closely resembled the hat we know today. Did you know that it wasn't even socially acceptable to wear a baseball cap outside of the field until the s?
The hat features a rounded, structured crown often with a button on the very top. Toward the front, there is an elongated bill.
Several sub-styles of the cap have emerged over the years. The trucker hat originated from the s as a promotional giveaway item from farm supply companies. It sports a single foam frontal panel, the rest of the crown perforated. This style is beloved by superstars like Lionel Messi.
The dad cap holts six panels around the crown, and is said to be named after the baseball cap's sudden popularity among dads in the 90s.
Finally, the flat-brimmed cap, or the snapback, is the trendiest of the lot. This one is used often by the younger crowd, and the flat bill is meant to convey a sense of newness.
The baseball cap is the most casual hat on our list. True to its athletic routes, it is only meant to be worn in the most laid back of scenarios. Do not take this into the office or a job interview, but enjoy it at the family barbeque.
Overview
As you can see, gents, the possibilities out there. Much like watches, hats can be a practical and stylish extension to your personality. You just need to pick your favorite.
In reading our recent Brief History of the Ballcap, I was reminded just how much I love the look of vintage-style baseball caps. There’s a simple elegance to their styling, making me long for those halcyon days before teams adopted kooky logos and zany colors, with specialty uniforms for St. Patty’s and every other remotely marketable holiday. And at least to my noggin, the fit of an old-timey cap is a lot more flattering, as most tend to follow the natural shape of the head.
We may indeed be living in the time of “Peak Cap,” as there are more companies than ever making these great hats. So here is—right over the plate in your sweet spot—what I believe to be the most comprehensive buying guide to vintage-style caps anywhere. Get ready, these are why you have a credit card.
Once upon a time, there was the legendary Cooperstown Ball Cap Co., and they made the finest—and to a large extent, only—vintage-style ball caps in the land (more on them in a bit). Shortly after they called it quits in , CBCC founder Will Arlt opened up the Ideal Cap Co., an outfit with a continued commitment to making great vintage-style caps, but a pared down selection to alleviate some of the headaches that went along with the wonderful inefficiencies of the Cooperstown process.
I wrote about Will back in , and he’s still churning out killer caps—every one made in the U.S.A.—adding a new style each month to his existing stable of Negro League, Semi-Pro and other more esoteric ball clubs. (Like every company in this list, you can get fitted sizes or a cap that’s adjustable. But c’mon, figure out your hat size and look like the champ you are.) If you can’t find an Ideal cap you can’t live without, you’re not looking hard enough.
Brooklyn Tip Tops, ($49). Courtesy of the Ideal site: “It was only two years after the Brooklyn Dodgers abandoned Washington Park for Ebbets Field that the Federal League set up business there as the Tip Tops. Had the league lasted just one more year the team had announced plans to play the first night games in . Navy Pinstripes on Gray Wool Body, Navy Flexible 2″ Visor, Navy Embroidered Logo.”
From its six-panel construction with a beautiful 13oz. athletic flannel to the hair canvas “stiffener” in the crown’s front to the leather sweatband, this cap is pure luxury. And the flexible visor means you can fold and jam it in your back pocket, forget you did so, drive to Hermosa Beach to eat fish tacos, and hours later retrieve it when you finally remember, the cap emerging all the better for the wear. Hypothetically speaking of course.
If you already own a vintage-style ball cap, chances are it’s from Ebbets Field Flannels. Not only has EFF been making high quality old-style caps since my sophomore year in college (a time historians refer to as ), but they’ve been a leader in the charge to popularize classic caps, and have also done tons of collaborations with brands big and small.
Founded with a commitment to “bringing the quality, beauty and craftsmanship of mid-Century American athletic garments to a 21st Century public,” founder and owner Jerry Cohen started the company by bringing in one bolt of vintage fabric at a time. There is a huge selection of great vintage team options, but my favorite is…
Brooklyn College Vintage Ballcap ($49). Ebbets Field Flannels says, Made in homage to “The Kid from Long Island,” Marius Russo, this cap harkens back to some classic times, but I mostly like it because my last name starts with a “B.” The Ebbets Field caps don’t fit as…contourly (a word I just made up) as an Ideal, but they’re less boxy than a New Era (more on them in a bit).
There is some overlap in terms of the team caps that each of these companies make, so you’ve got options depending on the silhouette you prefer. This American-made cap also drips fancy, with substantial maroon wool, a gold felt letter, EFF’s signature green satin undervisor, a horse hair buckram crown and a cotton sweatband. I doubt it’s intended to be folded and pocket-jammed, but I’m going to do it anyway the next time I’m craving fish tacos.
While it sounds like the tile of a gritty new HBO drama, American Needle is actually a Chicago-based needle-importer-turned-headwear-manufacturer with deep roots in the athletic apparel industry.
As they tell it: In , American Needle approached the Chicago Cubs with an idea of selling fans baseball caps like the ones the players wore on the field. The Cubs agreed to the proposal, with the team’s ownership at the time noting, “Who would want to buy the hats that the players are wearing?” The first run of Cubs hats sold out in one day and a second batch sold even faster. Talk about an idea with legs! These days American Needle makes a huge number of team caps in a variety of styles (curved brim and flat), and I simply couldn’t resist…
Pittsburgh Pirates Road ($31). What’s not to love? Adopting a nineteenth century pillbox-style cap (I know I keep saying it, but, more on that in a bit), the Pirates won the ’77 series on the road in this spectacularly gold and black cap. This beauty is a fitted wool-blend with a curved brim (though not too much), vintage replica logo in lofted embroidery, and a dark green undervisor.
Wearing a rounded nineteenth century style cap at the height of the disco era was a bold move, and for it the Pirates were rewarded greatly. I like to think the looks I get while wearing this cap are for having the same sartorial confidence…or perhaps I have guacamole stuck in my beard from having just eaten fish tacos.
You can’t talk ball caps without tipping your hat to the biggest of Big Dogs, New Era. To say they dominate the cap market would be a dramatic understatement, like suggesting I only “kinda’ like” fish tacos. New Era was founded in and continues to operate out of Buffalo, NY, my old college stomping grounds, and there’s little I don’t like that emanates from the Queen City (other than their annual 11 months of snowfall).
New Era found success right from their start in , and according to their site, By , New Era was the only independent cap maker supplying caps to big league baseball teams. In , Harold Koch (son of founder Ehrhardt Koch) designed New Era’s fitted 59FIFTY style cap, giving it a more contemporary look. Given that, “more contemporary look,” most wouldn’t immediately think of New Era when looking for a vintage-style cap, but they do offer a selection of old teams. And if you grew up in New Era caps and love their more square, structured look, then there’s a cap just waiting for you (just please take the sticker off the visor). Plus, they even make minor league team caps like…
Buffalo Bisons Sunday Cap ($29.99). If you ask me, the closest you can get to experiencing “vintage-style” baseball today is by taking in a minor league game. There’s usually plenty of seats available (and you won’t need a second mortgage to take the whole family) where you can sit and watch guys who’ll still run out a grounder to first.
I dearly miss Bison baseball, and even more so a night game feast of a fried baloney sandwich and a Big Ditch IPA. (If they served fish tacos, I might consider buying a snow blower and moving back.) This is the cap the Bisons will wear for all Sunday home games, and I’ll loyally follow suit from miles away.
Unless it’s an especially busy time when she brings in an extra pair of hands, when you order a cap from Stockbridge Sewing Works, it will be lovingly and meticulously made by Norma Hildebrand in Hanover, PA (Stockbridge is her maiden name). Norma studied at the old school of American textile manufacturing, learning a thing or two or a hundred and fifty-three about quality, craftsmanship and a maniacal attention to detail.
Back in the early s, Norma was one of a small, elite group that Will Arlt of now-Ideal / then-Cooperstown Ball Cap Co. trusted to hand-make caps bearing his tag. In fact, when Cooperstown closed up shop, Will offered many antique sewing machines to Norma for the price of, “come and get ’em!” She’s been making caps on those machines ever since, and these days is at the height of her powers, offering a true custom experience.
Without exaggeration, if you can think it up, she can make it, no matter if your head is teeny tiny (like mine) or more befitting the top of a Thanksgiving parade float–sky’s the limit. Any while Norma doesn’t have any licensing deals with major sports leagues (and thus, offers no “official” team logos), if your last initial is “D” and you’d like it in white felt or embroidery in Old English script on a navy cap, well, who is she to argue with one’s monogram and color preference? Norma encouraged me to dream big, so I snagged…
The Caps:
Chicago-Style Pillbox, and 60’s-Inspired Six-Panel Alternate-Colored Front ($45, $53). The Chicago-style pillbox hat is a style that harkens back to the ’s, when round caps were a popular choice for the pioneers of early baseball. (Ideal offers caps in this style as well.)
What’s great about Stockbridge is, as long as Norma has the material in stock, you can have any color or number of bands or length of visor you please. I went with gold white and navy in wool flannel, with a leather sweatband (natch) and 2″ visor. I love it, in part because no one else has one.
The same can be said of the royal, gold and white number, my initial in “shadow” felt letters, 2.5″ visor. The color combo is a nod to the defunct Seattle Pilots, but again, unless you’re looking at me shoveling tortillas stuffed with mahi-mahi down my craw, you won’t see one like it anywhere else.
For a truly one-off, handmade custom cap (six-panel, eight-panel, five-panel, four-panel, historical styles!), Norma’s prices are the deal of the century. (And if you happened to miss out on our limited-run Quint Hat, Norma makes one that’s nearly identical.)
It was a dark day in when this passage appeared on the Cooperstown Ball Cap Co. website: Regrettably, after twenty-three years of making fine historic replica ball caps, Cooperstown Ball Cap Company has discontinued operations. Commercial, financial and legal difficulties; and the complexity of sewing one-of-a-kind caps in the U.S, make this decision inevitable. We thank all our customers for whom, over the years, we have been pleased to make a true vintage ball cap.
My friend Ramon “let” me steal my first CBCC cap from him back in college (-90?), and I was immediately hooked. (I’m wearing it in the awesomely unflattering old photo below–no white in the beard!–drooling beneath the crown of a Birmingham Black Barons cap, Satchel Paige’s old team.) CBCC was known for their hand-drawn catalogs, encyclopedic offering of teams and styles, and for setting the standard by which all future vintage-style caps would be judged.
Soft crowns were a revolutionary reintroduction to the market, exposing baseball fans and fashion icons (many catalog covers were drawn by artist and one-time GQ contributor Richard Merkin) to the wonders of the wool flannel cap. (Heddels alum and Archival Clothing writer Lesli Larson wrote a beautiful lament to CBCC here.) Since many folks way smarter than I bought a ton of CBCC caps for collecting, there are a surprising number of them for sale out there on sites like eBay, Etsy and even Grailed. There’s one less in circulation, as I just scored…
Cuban X Giants. I was lucky to find this early ’90’s NOS cap in my size, a hint faded but in perfect shape, save for a few tiny “flea bites.” The X Giants were a Negro League team from to , and this cap is historically true to form with a shallow six-panel (horse hair “stiffened”) crown, sewn-on felt “X” in orange and black, and horsehide leather sweat.
Due to the (who knew?) “edgy” nature of the letter “X,” this hat was trendy for a while and made by a number of companies, but none comes close to the authenticity and soul of this CBCC original. (I can’t find my old BBB cap–I will not rest until I do–but you can still get one just like, made to the same specs, from Ideal.)
When discussing an early draft of this article with my dear friend Jon (equal parts baseball and hat fan), he told me about an old umpire cap he wore all through high school. Since all the caps in that draft covered what players, coaches, managers and fans wore, I thought it would be fun to see if anybody was still making a vintage-style ump’s cap. Anybody is, and they’re the family-run Richardson Sports of Springfield, Oregon!
As their site says: We will be an outstanding corporate citizen, respect and preserve the environment, and give back to our local community. We will never cut corners to save money, nor will we sacrifice our ethical code for personal gain at the expense of others. I. Love. That. While today’s umps wear an “athletic” uniform of sorts and a generic black, dare I say “dad hat,” there was a time when they sported black suits, white collared shirts with ties, and a nifty short-visored wool cap just like this one! Richardson makes all kinds of contemporary ball caps, but in my opinion none finer than this…
1.5″ Visor, 3-Stitch Plate Umpire Cap ($11.95). While not a soft crown, this wool-blend cap hugs the head like nothing I’ve ever worn (somewhere between a jockey and cycling cap), and the super short visor (so it won’t get bent under a mask) gives it a look unique to hatdom.
Wearing any of the caps from any of the companies featured here will definitely set you apart, but nothing to the extent that will this snazzy number, available in black or navy. Isn’t it time we give the umps some love? They’re out there and behind the plate, providing guidance and order in a world gone mad. Wear this to the ballpark and show your appreciation…you know they’re just callin’ ’em the way they sees ’em.
And when you do get yourself one (or 37) of these caps, the best way to fully embrace their old-timeyness is to wear the Hell out of it! Just look at the lid on the above past manager of the Toledo Mud Hens. It clearly has a golf ball-sized hole in the right side of the crown. And he’s posing for a picture in it! Did his cap fall off during a bench-clearing scuffle…tear on a rusty nail in the locker room…get caught in the bus door at the start of a road series?
I guess we’ll never know, but of one thing we can be sure–the appeal of an old style ball cap gets better with age, even when well-ventilated. In a time when every major leaguer can wear a new cap in every game of the season (and you wonder why a family trip to the ballpark has become a triple-digit experience?), it’s nice to don a new cap from the old days when you got one for the whole season. And next.
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