
Up until the 1950′s men were rarely seen out and about without a hat sitting upon their head. Since that time, the wearing of hats has seen a precipitous decline. No one is precisely sure why. Some say the downfall of hats occurred when JFK did not wear a hat to his inauguration, thus forever branding them as uncool. This is an urban myth, however, as Kennedy did indeed don a hat that day. Another theory posits that the shrinking size of cars made wearing a hat while driving prohibitively difficult. Most likely, the demise of hats can simply be traced to changing styles and the ongoing trend towards a more casual look.
Yet hats are due for a full resurgence. Hats are both functional and stylish. They can cover a bad hair day, keep your head warm, and shade your eyes from the sun. They can also be worn to cover a receding hairline, which interestingly enough is why Frank Sinatra, an iconic hat wearer, start wearing one in the first place. They give you touch of class and sophistication, impart personality, and add an interesting and unique accent to your outfits. And hats are a sure-fire way to boost your confidence. A cool hat can quickly become your signature piece and give you extra swagger.
Of course men today still wear hats, but they are most often confined to ratty baseball caps, hippie beanie caps, or the thankfully almost extinct trucker hat. There is nothing wrong with these kinds of headpieces per se, but there are other hat options out there. So mix up your lids with these various options:
The Flat Cap

Photo by Menno Ophelia
The flat cap has a rounded shape, a small brim and a high back. Long associated with working class men in the UK, the flat cap can be a stylish way to add interest to a casual outfit. They can give your tired jeans and t-shirt look some unique style. Choose the more masculine flat cap over the similar, but rounder and puffier newsboy cap. The latter has been almost entirely co-opted by the ladies.
The Fedora

Fedoras were once considered de rigueur for men going out in public and a necessary accessory to formal and business attire. While once mainstream, a man in a fedora is now seen as a trendsetter. Fedoras are soft, usually made of felt, creased lengthwise down the crown, and pinched on both sides. Obviously you cannot pair a fedora with jeans and a polo. They are only an appropriate accent for dressier outfits. But the pay off-loads of style, class, and confidence-make dressing up worth it. Fedoras will make you look manly and a bit mysterious. Worn by Prohibition era gangsters, almost all of the movie stars of the 1940′s, and Old Blue Eyes himself, donning a fedora puts you in touch with a truly luminous and manly heritage.
The Porkpie

Photo from The French Connection![]()
Named for its resemblance to an actual pork pie, this hat is similar to a fedora but with a flat top instead of a pinched crown. The brim is also shorter and turned up. The hat is often associated with the jazz, blues, and ska culture, but was also worn by the likes of Robert Oppenheimer, father of the atom bomb.
The Homburg

Photo from The Godfather
The Homburg is another hat similar to the fedora. The Homburg’s brim lacks the fedora’s pinches, and is turned up all the way around. The hat is accented with a hatband into which a feather may be stuck. Less casual than a top hat, and dressier than a fedora, the Homburg was the go to lid for politicians and diplomats in the 20th century. Favored by the Godfather and resurrected by the likes of Snoop Dogg and Tupac, the Homburg now carries a distinctly gangster flavor.
The Bowler/Derby

Photo by Lainey’s Repertorie
Bowlers are hard, made of felt, and have very short brims. While considered a British icon, the bowler was also part of the urban culture of America in the 19th century. For example, one of the gangs that roamed the mean streets of New York City around this time were the Plug Uglies. The Uglies were never without their bowler hats which they wore both as their signature piece and to protect their heads during their many scuffles with rival gangs.
Wearing a Hat

Cock your hat–angles are attitudes. ~Frank Sinatra
Hats can give you a feeling of effortless cool and manly confidence. Few people loved hats more, or wore them better than Frank Sinatra. He was constantly playing with the idea of angling and tilting his hat to convey different attitudes. Here’s how Frank wore his hat to reflect his mood:
- Wear your hat pushed back to seem more open and accessible
- Tilt your hat over your eyes to seem mysterious and intimidating
- Tilt your hat up 1 inch from completely straight to project an all-business attitude
Hat Etiquette
In adopting the hat as your signature piece, you must also accept the responsibility of hat etiquette. Often ignored, hat etiquette will show that your uniqueness extends not only to you choice of headwear, but to your manners as well.
- Promptly remove your hat upon entering an elevator, restaurant, or someone’s home. Never wear your hat during a meal.
- Touch the brim of your hat lightly when greeting a friend.
- Raise the hat by the crown when meeting a female friend in public.
- Remove your hat during the national anthem and place it over your heart.
Header photo by Edieamber
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Picking a hat is most important. Don’t go for a specific style. Find one that fits your personality and face shape. Best way to decide if it fits you or not is to look in the mirror and decide if you see YOU, or you with a hat. Some people try to pull of these hats and it makes it look like the hat is wearing THEM.
It’s just advice.
I hunt almost every season, during small and upland game hunts I have my fedora on. It takes me back to hunting with Grampa he always had his cowboy hat on. The rest of the time its a old beat up Cabelas ball cap.
Top hat?
Hey, you seem to have forgotten Top Hats, the most iconic hat used by Americans. Even used by the Man himself, Abe Lincoln!
Worthy article.I love my hats,mostly fedora’s.Note my e mail name.Thought the comment on bringing back the codpiece was interesting.Wouldn’t work well with my kilt.Tony
Making a tricorne hat. Inspired by AC3.
Thanks for the info. Suggest you add: Never tip your hat to a bloke, particularly not an older one.
Aren’t you supposed to take the hat or cap off when you enter a public building- school, courthouse, etc.? People do not do that anymore (amongst other things).
As someone who owns and on occasion wears a top hat. It’s a pain in the ass to put on a hat for formal events. Take it off upon entering and along with my gloves worry that some no class havin sketchy lurker walked with them. While I danced with my wife. So I now leave my top hat at home.
It must be already ten years ago since I bought my first had (I was about 23 years old then). Now I wear a hat all the time, it became my trade mark. I think I have about 20 hats by now, mostly fedora and homburg style. For the summertime I have a couple of so-called Panama hats. I can’t imagine going out the door without a hat on my head…
I haven’t really been a “hat guy,” but lately, I’ve been wearing a Russian-style fur hat I got as a gift, since it’s getting cold in Michigan. I’d like to start wearing more, but I don’t know what I should get for a first hat, or where to start looking for one.
By the way, there is a wrong way to wear a hat — just look at http://youshouldntwearthatfedora.tumblr.com/
Am a hat guy too.
Am glad you said ” crappy baseball cap.”
It seems like people wear them everywhere!
I thought you suppose to wear them to support your team,AT THE GAME.
A friend of mine tried to wear a black baseball cap with a tux. Anyway-hats off to you!
I hunt almost every season, during small and upland game hunts I have my fedora on. It takes me back to hunting with Grampa he always had his cowboy hat on. The rest of the time its a old beat up Cabelas ball cap.
I used to don ratty baseball or a good beanie on “hat days”. Because of this article and the resurgence I’ve seen just in my town, I’ve purchased my first two flat caps and wear them with pride! Great article and better caps!
I’m all about the resurgence of hats, and resurgence of a lot of things.. but let’s don’t forget to take them off indoors, including baseball caps! It’s not nostalgic nor fashionable if you can’t do it with the class of our hat-wearing forefathers.
I always wear a hat , but more of a Cowboy style hat. I noticed they weren’t mentioned in this article ?
I hate baseball caps , I have several that were given to me and don’t wear them. I prefer a good cowboy style hat with a leather chin strap because the wind out here will blow most hats off. :)
So I have been greatly inspired to bring back the hat and I have been working on it for some time now. I follow all hat etiquette except for the part on removing my hat when I enter homes, meals, etc. I would except I get this horrendous hat hair. Any way to avoid this?
What about a beret? Not the military variation, but the one used in France or Spain, or by Basque shepherders. Classy and cultured look.
I bought a wool flat cap a year-and-a-half ago and have been wearing it quite a bit. Sometimes I want to wear a hat and don’t want to dress like an adolescent. By the way, is there any headwear more heinous than the baseball cap with a perfectly flat brim (with or without various MLB and manufacturer stickers still affixed)?
In Texas, the cowboy hat is still the hat to wear. Worn low, just above eye-level, is the douche-bag trend these days, though I hope cocked makes a comeback a la Roy Rogers and John Wayne. Always remove your hat inside a home, church or workplace, and remember your seasons: dark felt hat after Labor Day, light (straw) hat after Easter.
I’m 19. Myself and three of my friends wear hats nearly every time we go out. I’ve got quite a few, and only one is a standard ball cap. And most of these very unique hats have come from Goodwill stores.
Hopefully my generation realizes that proper hats, in the right shades, are excellent. Fashion is such a silly thing.
What about the Aussie Akubra?
I wear one of these day in day out as do all my farming mates. They also have the added bonus of lasting forever.
I favor the comment someone made one time at The Fedora Lounge: something like, “When I attend a baseball game I don’t dress like a baseball player, I dress like a baseball fan.” So, whe I go to the ball game I dress like a fan from the 1930′s.
I’ve been looking for a semi-formal hat for a while, but local stores have a very limited selection… any suggestions for online stores or shops near southern Indiana?
Regarding the top hat, that’s seen exclusively with formalwear/ evening attire, if at all nowadays. So I can see why they’ve omitted that one from the article.
As for the hats-off rule, I always remove mine whenever I enter any building. Hats are there to serve a purpose; I’ve no need for protection from rain, snow, or sun indoors. It just looks silly and out of place indoors at all, not just in an elevator or home.
I prefer a western style. I refuse to call it a cowboy hat due in part that the hats of the old west were many and not all “Cowboy Hats” were worn by Wranglers, Ranchers, or Livestock Men. Some were worn by Career Gamblers, Bankers, Teamsters, Wells Fargo Men, Railroaders and the like. So for me it is the Resistol Chute 5 style in Black with a Custom leather band. In real day to day life I am a Railroader by trade how manly is that for occupation. No pun intended we now share our ranks with the ladies…
However when not working I consider myself the Gambler, not the poker playing kind just a Gambler figure we all kind of gamblers since we roll the dice everytime you get behind the wheel of our vehicles and share the highway with other gamblers… Lifes a Gamble and if I lose I want to be in my best hat….
P.S. @ Work I still occassionally break out my trusty ol’ Pin Stripe special when in the mood. Bringing back old flair to new things is my passion….
You forgot my three favourite types of hat: the beaver and silk toppers and the boater.
These days the two top hats are only ever worn with morning and evening suits and so are worn with white tie. With morning dress people normally wear beavers or bowlers, although it’s rather open to personal tastes; with evening dress, an early type of black tie, it’s always a beaver or silk topper and with white tie it has to be a silk topper.
As for the boater it’s just a massively stylish, to state my own views, semi-formal cool summer straw hat that resembles a pork pie.
I didn’t read all of the comments but we Orthodox Jews may be the last Americans that continue to wear fedoras on a regular basis. Like any sub-culture, the details can e very telling. Baltimre. Brooklyn, Lakewood New Jersey ( to name just a few) have their own subtleties of tilt, crown, brim etc. Kudos on a great article.
‘Hats maketh the Man’. You can wear a hat with any occasion and with any outfit; be brave! And don’t feel your too old to wear certain hats; if you like it,your never too old.
I have every type of hat and adore them (at least 45!)! And probably will till I die!
I have a number of hats and enjoy wearing them. There is something about being in public in a hat. I notice people you interact with look at you more directly when communicating. Hats are cool. Nothing worse than a topless man. Love the article.
Some here have referred to it as a top hat, but Abraham Lincoln more accurately donned a stovepipe hat. Our 16th president’s hat was beaver pelt, and if you have a chance to view one of his originals, you can view two worn spots on the top as a result of Abe’s hat-tipping the ladies.
Personally I wear an Oilcloth Aussie, bought as part of a costume a few years ago and never managed to put it down. It’s my trademark now. People recognize the hat, whether its in a store, on the street or driving down the road. It’s a part of me now. Just this past evening, leaving a restaurant an older lady stopped me and my companion to comment that I wore my hat well and how right it looked.
That, is the kind of hat you should look for, whatever type that may be.
I prefer cowboy hats. Great sun and rain protection. I have a black felt one and a white straw
Cheers, enjoy your site. I used to wear a flatcap (yes to hide my messy hair) when I was a musician. I remember how many elder men wished me as I walked past them when I was traveling across Canada. I was very young then, but it certainly attracted a lot of respect from the older classier gents. Today I am part of that older gent, and I just picked up a hat which I , through your site , now know it ‘s a homburg. Now, I know , at last, after many years what Procol Harem was singing about with the song of the same name. I used to think Homburg was just another city like Hamberg, lol. I suppose I am older now, and I should know better, huh? Happy Spring Equinox, and cheers from Canada.
A rather interesting website, I applaud those who are making an effort to bring back proper male manners. As far as the hat goes, I have been wearing fedora’s and the cattleman’s hat since was in my teens. I grew up in Kansas and Texas. There is a sense of dignity in wearing a hat. In formal occasions I wear the Fedora, felt in winter and a straw version in summer. The western hat, I wear in both casual and work. I like clean crisp lines. My jeans will be pressed as well with a crease as It dresses them up. I agree with the hat protocol but would like to add to it, noting that a man should remove his hat when he meets or is introduced to a female. Manners are hugely important, and are mostly lost. You simply stand out now a days just by employing common courtesy and manners. Are table manners covered here? From what I have noticed many do not know how to eat at the table, might be a nice article for this site.
Finally, the hat is coming back. My father was never without a fedora even when it was not “in”. I have been wearing them for years and am pleased to see them reappear. It is great to find them in the stores again.
More on hat etiquette please. I was raised that men should ALWAYS remove hats when indoors, I’ve seen plenty of fedoras being worn in bars, shops… just seems wrong. Might be a good subject for an article.
Great article! Remember to find a hat that’s of an appropriate size. IMO, nothing looks more ridiculous than a guy who wears a hat that’s too small for his head…
Clint, you might try Henry the Hatter. Great store here in Detroit. They have an online store as well. Great old-fashioned place; stop in if you ever get an opportunity.
https://www.henrythehatterdetroit.com/
awesome hats indeed.
I started wearing hats when the inevitable bald spot appeared. I walk to work and though temperatures here rarely go below -5 centigrade in mid winter a flat cap or almost anything is great. I’ve attended many car club concourses and a baseball cap does not cut it when you’re showing a classic Mercedes. So out comes the beige cotton Fedora or a grey felt hat with broad brim and pork pie style crown, plaited leather band. Complimented by two younger ladies when I first got it, BTW
My mother used to say “The broader the brim the smaller the sheep station.” (ranch).
The Homburg was considered more formal than the Fedora but appears to have derived from hunter’s hats . There are details over at the “Gentleman’s Gazette” site.
A small business in Donegal Town, Ireland makes wool flat caps to order or chose from their range, Google them
The cowboy hat wasn’t mentioned – aside from the urban enclaves who can’t believe they actually ARE in the west, if you’re west of the Mississippi, a cowboy hat is appropriate in most places.
And why not wear them east of the Mississippi too?
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