A Guide to Men’s Hat Styles

May 5th, 2015

Hats are slowly becoming a daily accessory for more and more modern gentlemen, reminding us of a time in America when men wouldn’t leave the house without one.

Men’s hats come in many shapes, sizes and fabrics. So to make it easier for you, we’ve broken down the basic hat styles, offered a little background history, and provided some pointers for adding them to your wardrobe.

The Fedora


A fedora is typically creased lengthwise down the middle of the crown, then “pinched” near the front on both sides. Fedoras have become widely associated with gangsters and Prohibition, which coincided with the height of the hat’s popularity in the 1920s to early 1950s. They were a daily accessory for many American men until JFK, a style icon in his own right, started making public appearances sans-chapeau and started a 40-year trend toward general hatlessness.

A good felt (or straw) fedora has a sturdy but flexible brim that can be “snapped up” or “snapped down” in the front or back, allowing you to mold the brim and achieve the perfect, slightly-askew shape. My favorite are unlined and crushable. Find one in a quality lightweight felt (probably a versatile shade of brown) with a brim that’s roughly 2.5″ wide (depending on the size and shape of your face), then start working on perfecting the subtle side tilt (RIP MJ).


The Homburg


The fedora’s dressier cousin, the homburg, also made primarily of fur felt or straw, is a good choice for a formal business look. It has the same center-creased crown as the fedora (although sometimes not the side pinches), but the brim is stiffer and has an upturned lip all the way around (which usually cannot be molded or “snapped down”).


The Trilby


The trilby has a shorter (thus narrower) brim which is angled down (“snapped down”) at the front and turned up at the back, versus the fedora’s wider brim which is more level and flat. The trilby also has a slightly shorter crown than a typical fedora design.

It reached its zenith of common popularity in the 1960s; the lower head clearance in American automobiles made it impractical to wear a hat with a tall crown while driving. It faded from popularity in the 1970s when any type of men’s headwear went out of fashion. They had a moment of rise with 90’s boy bands and cheesy musicians, but lately they’ve landed closer to being a symbol of nerd culture, especially cheap versions made of synthetic fabrics.


The Porkpie


The porkpie has a narrow brim that is always turned up and a flat top with a circular indent. As fashion writer Glenn O’Brien once joked; “the porkpie hat is the mark of the determined hipster, the kind of cat you might see hanging around a jazz club or a pool hall…it is often worn with a goatee, soul patch, and/or toothpick”. The most famous porkpie in recent television history is worn by Bryan Cranston‘s character Walter White in Breaking Bad when he appears as his alter ego “Heisenberg”, whose persona is largely associated with the hat. 


The Panama


The Panama hat is a traditional brimmed straw hat of Ecuadorian origin. Similar in shape to the trilby (down in the front, curled up in the back), but with  proportions more similar to the classic fedora. Traditionally Panama hats were made from the plaited leaves of the Carludovica palmata, a palm-like plant rather than a true palm.

The rarest and most expensive Panama hats can have as many as 1600–2500 weaves per square inch. These hats are known as Montecristis, after the town of Montecristi, where they are produced. The Montecristi Foundation has established a grading system based on a figure called the Montecristi Cuenta, calculated by measuring the horizontal and vertical rows of weave per inch. A “superfino” Panama hat can, according to popular rumor, hold water, and when rolled for storage, pass through a wedding ring.

Although the Panama hat continues to provide a livelihood for thousands of Ecuadorians, fewer than a dozen weavers capable of making the finest “Montecristi superfinos” remain. Production in Ecuador is dwindling, due to economic problems in and competition from Chinese hat producers. Our friend and favorite LA hat maker Nick Fouquet explored the gradual extinction of this cultural tradition during a recent trip to Ecuador, as capture in this video.


The Boater


The boater is a men’s summer formal hat made of stiff sennit straw. It’s characterized by it’s inflexible brim, flat top, and wide grosgrain band (which is often striped, or solid black for traditional summer formal occasions). Similar in formality to the homburg, a boater is correctly worn with a blazer, smart lounge suit, or even with black tie (as seen here by the one and only Dandy Doctor Mr. Andre Churchwell).


The Wide Flat Brim


A cross between a wide-brimmed fedora and a western country hat, the large, stiff, flat brim is the trendiest hat in menswear right now. These heavy beasts are the opposite of the crushable/packable hat. They are stiffened and made to hold their artistically flat shape, no matter what.


The Newsboy


The working man’s cap. Flat caps were very common for North American and European men and boys of all classes during the early 20th century and were almost universal during the 1910s-20s, particularly among the working ‘lower’ classes. A great many photographs of the period show these caps worn not only by newsboys, but by dockworkers, high steel workers, shipwrights, costermongers, farmers, beggars (such as Oliver Twist), bandits, artisans, and tradesmen of many types. This is also well attested in novels and films of this period and just after.


The Driving Cap


The Ivy cap, or flat cap, is similar to the newsboy, only without the floppy 8 panels and the button on top. This style, which traces its history from Southern Italy, Northern England, and parts of Scotland, also wins the awards for the most names. It is also referred to as a cabbie cap, longshoreman’s cap, cloth cap, scally cap, Wigens cap, ivy cap, golf cap, duffer cap, driving cap, bicycle cap, Jeff cap, Steve cap, Irish cap, Paddy cap…in Scotland as a bunnet, in Wales as a Dai cap, and in England and New Zealand, as a cheese-cutter.

Cloths used to make the cap include wool, tweed (most common), and cotton. Less common materials may include leather, linen (as pictured) or corduroy. The inside of the cap is commonly lined for comfort and warmth.


The Baseball Cap


Time to grow out of the snapback with the flat brim and the stickers still on it. It probably wouldn’t be a back look to lose ant heavy sports memorabilia from your casualwear altogether. Think about a baseball cap that is a little more discreet, mature, and versatile – like this simple worn-in cotton cap by our friend Josh Woods.


The Beanie


This one is pretty straight-forward. Wool or cashmere, usually. Keeps head warm, not great for keeping hair in place.


As men, we wear a lot of hats… What’s your go-to style? Feel free to share in the comments.

Thanks, as always, for reading. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop

  • Ronnie the Boy Wonder

    Try a Elósegui, Super Lujo” Beret outer size diameter 31.75 cm if you have a 60cm head size aka XL. These are the real deal and at that size can be worn in several ways as there is a lot of material you can pull around.

    Waterproof and keeps the sun off you, and unlike a stupid baseball cap or worse a cowboy hat, the wind wil not blow up it off. A joy to fish with, beach, ferry rides, any place windy.

    If you get one without a leather band, recommended, you will have to hand stretch it to fit as they come only in one head size, it will be small.

    You can find a YouTube video on how to do this. You basically pinch it with thumbs near each other on the band and pull over and over, slowly working around it. You want to pull the fibers sideways along the fabric band.

    Never pull from opposite sides like a rubber band.

  • Eric

    Can someone tell me who made the straw hat shown in example of a Homburg?

  • cleo48

    My wife told me to start dressing my age. I chose 1904. Among other things, I bought a set of button down vests, and a well made grey bowler.

  • TJ

    Where are the derby and top hats?

  • Natalie Grace Lein

    Thanks for this! I’m an artist and might be stopping back to get some reference for future projects. Love this site!

    My husband and I were watching the Masters, trying to figure out what you call that old-school golfer’s cap. After reading this and a few articles, I told my husband he might as well just call it what he wants and he’ll probably be right somewhere. ? I’ll just call it a flat cap, I suppose.

    – Natalie

  • http://www.sexyshe.in/ Deepti Singhal

    nice collection, well displayed

  • GuyFawkesIsAlive

    Just bought my first beaver felt top hat. It looks so dapper and have received all kinds of comments from women and men alike.

  • Patrick Proudlock

    In the States, knitted men’s cap is called a beanie. Never in Canada; it’s a toque. (pronounced like the number “two” with a “k” sound at the end.)

  • The Art of Shaving

    Always a big fan of the newsboy and driving caps! You get the right groomed facial hair on top of that and you’ll be looking quite dapper!

  • Hamza Bilbeisi

    My mother bought me a beautiful navy felt fedora a few years back, except I never appreciated good headwear – and, being a young teenager, I thought it was lame my mom was buying me clothing. After lurking around on this site for a while though, and seeing the fedora pop up from time to time, I’ve really started to appreciate a good hat! Thanks as always

  • Harrison Krupnick

    Fantastic article, AOS! I love Nick’s hat. Wish I could pull it off.

  • Brett

    I would love to find more information on how the various hat styles should fit. Without access to a knowledgeable haberdashery nearby, I am often stuck going with what seems “right;” however, as with all things style, I am sure there are rules and guidelines for finding that perfect chapeau. Perhaps a follow-up article?

  • PeterK1

    What style of hat do you recommend for us guys with very small heads? Honestly, my 4 year old son and I can trade hats.

    I like Fedoras (stingy brim) and driving caps but it’s hard to find ones that fit me.

    • http://www.TSBmen.com/ Dan Trepanier

      Whoa! I would suggest shopping the kids section of the hat shop (probably save some $$), since it’s all about size and proportion. Visit a shop that has a lot of styles to chose from and try as many as possible until one flatters your child-sized dome. I would also keep the tailoring slim and the overall padding minimal… Cheers mate.

      • PeterK1

        I think I exaggerated the smallness of my noggin. My son has a big head. I will check child sizes but in my neck of the woods there are few hat shops and they don’t seem to carry smaller sizes.

        Any hat makers that make nice hats in small sizes or clothing stores that carry small size hats?

  • TO

    Right now my approach to hats is if I’m having a bad hair day, or if I have shampooed my hair that day and it’s all poofy, then I’ll wear a ball cap to cover it that day. Otherwise I’m paying my barber about a $1/day so I’ll let his work shine the rest of the time. I avoided a toque pretty much all winter for this reason, even to the surprise of myself.

    If I invested in a nice classic hat though this attitude might change and this guide is a real awesome and thorough resource about the different styles!

    • http://www.TSBmen.com/ Dan Trepanier

      Go for it TO, you got the cojones.

  • Miguel

    I prefer Fedoras for all year long and Panama hats for S/S or vacations.

    • http://www.TSBmen.com/ Dan Trepanier

      Can’t go wrong there.

  • AdamE

    You can tell that Dan has been living away from the motherland for too long… Calling that hat a beanie may cause you problems next time you try to cross the boarder… It’s a Tuque….

    • http://www.TSBmen.com/ Dan Trepanier

      Haha. It will always be a Tuque in my heart.

    • DrFrost

      Man I’m Mexican, no one is go is going to care if you call it a beanie. Grow some cajones man, they probably won’t even know what you’re trying to say.

      • Rex Decker

        You called a dudes balls “cajones” because of your Mexican heritage, but you are remarking AdamE’s shouldn’t care that it is called a tuque in his culture (which I’m guessing is Canadian)?

    • Anon ymous

      Holiday in Cambodia by the Dead Kennedys was written for people like AdamE. So you been to school for a couple of years, and you think you know it all . . . . . .Playing ethic jazz on your 5 grand stereo . . .

      • Rex Decker

        What does calling it a Tuque have to do with schooling? That is what they are often called in certain regions, like in Canada. Calling it a Tuque isn’t pretentious. It has to do with the individuals culture. Kind of like the Mexican @DrFrost calling balls cajones.

        • Manu Zolezzi

          Except our Mexican friend can’t even spell it right. It’s cojones. Cajones is just drawers, as in where you keep your underwear.

  • Justin Faulkner

    Amazing article, Dan. Your insight is always appreciated!

    • http://www.TSBmen.com/ Dan Trepanier

      Thanks Justin. Your support is always appreciated as well.