My Hat Collection: my guide to male headwear

Back when we were in lockdown during the covid pandemic in 2020, I felt the walls were closing in. It was easy to slide into the dark corners of your mind during those days. That’s when you should find something you enjoy and be absorbed in it. Your soul will thank you. I’ve been collecting hats from different parts of the world for many years now. Partly, that’s because I’m bald and I need a head covering, but mostly it’s because I just love the beauty of a superbly designed lid. I also like hats that have stories attached to them.

So I started cataloguing my hat collection and making notes about each style. I update it whenever I think about it or get a new hat. So here are some photos of my hat collection along with my guide to male headwear. I hope you see something you like.

The Basque Beret

Apparently, they’ve been wearing berets in Northern Europe since the Bronze Age. The Basque-style beret was the preferred headgear of shepherds from the Aragon and Navarra regions between Southern France from northern Spain. As a result, by the 20th century, berets were associated with the French and Spanish working classes. They’re made from wool, felted to make it water resistant. The crown is turned inward at the edge and fitted with a leather band. Modern versions are often lined with satin.

Mine is a black beret topped with the traditional short stem (made in France by Cipan), which pretty much epitomizes the stereotypical headwear of all Frenchmen. I can’t wear it without someone saying, “Ooh la la.”

The Bobble Hat

The British bobble hat (also known as bobble cap or Bob Cap) is a knit cap (see below) that has a yarn “bobble” or pom-pom on top.  Along with the anorak, the pin-on rosette and the club scarf, the bobble hat was standard wear for English working class football fans back in the day. But then bobble hats got a surprise boost in popularity by the Geek-Chic trend, which turned them into a luxury designer item with a real fur bobble.

I only bought mine because, surprisingly, it is emblazoned with my initials. When your name is Michael H Frost and you see a bobble hat in a store with “MHF” on it, well, you buy it.

The Braid Trilby

A braid hat can be of any style, but made with the custom woven Toyo braid. They are a variation on the panama hat, which was made from plaited or braided leaves, bleached white, and topped with a silk band. Like the panama, a braid is lightweight, breathable, easy to wear, and perfect for tropical destinations.

Mine is a modern trilby silhouette made by the legendary hatmakers, Bailey of Hollywood, founded by George Bailey in 1922. Scroll down for a further description of the trilby. I bought this one in a mall in Long Beach, California, on my way to a vacation in New Orleans. If you’re after a hat, you’d have trouble going past the extensive range at Bailey’s.


The Bucket Hat

Bucket hats made a comeback in the ’90s, going from a humble fisherman’s hat to hipster cool. Made from heavy-duty cotton fabrics such as denim and canvas, or wool blends like tweed, bucket hats feature a wide, downward-sloping brim that resembles an inverted bucket.

My bucket hat is a khaki version made by the nautical shoe company Sperry. I don’t know much about shoes, but apparently Paul Sperry made his name back in 1935 with his boater-style footwear. Since then the Sperry top-sider brand has ended up on all kinds of boating apparel, including hats like this one.

I found it in a store in Florida, but had second thoughts and put it back. Older guys in bucket hats look more like humble fishermen than hipsters. Later, however, I saw a very dapper-looking dude wearing it around the shop and it looked good on him. I was filled with shopper’s regret. But then, while we were both lined up at the counter, he had second thoughts and discarded it on a nearby shelf. The rest is (personal) history.

The Derby

I bought this bad boy at a haberdashery store on Congress Ave in Austin, Texas, with my mate Lance Ford, and it’s one of the best in my collection. Lance took me there knowing I’d be in seventh heaven.

London hat-makers Thomas and William Bowler might have invented the hat named after them, but the American Wild West perfected it, which is why you’ve gotta go to Texas to get the best. The Texans call them derbies, and they were hugely popular in the 19th and early 20th centuries, worn by everyone from Butch Cassidy to Stan Laurel, and from Charlie Chaplin to A Clockwork Orange and Cabaret.

Admittedly, there are limited opportunities to wear a derby today. I tend to pull it out for weddings. But no serious hat collection is complete without one.

This one is 100% felt wool, with satin lining. Made in the USA by Scala with felt sourced in the Czech Republic.

The Fedora

This is one of my most worn lids. I’m really fond of it. I bought it in a vintage store while I was mooching around Cape Town, South Africa, with my friend Alan Hirsch, four or five years ago. It’s a Pierre Cardin velour plaza, branded by Hariton’s Men’s Outfitters in Wynberg (which, incidentally, is Alan’s home town).

The fedora is sometimes confused with a trilby, but they are a bit different. Fedoras generally have a wider brim than the trilby, which has a taller crown, and is frequently worn on the back of the head.

Back in the day, the fedora used to be uber-stylish, but these days it’s often associated with 1920s gangsters and tourists in cheap straw versions (ugh). So, if you’re gonna wear one, please wear a really good one like this. And when you do wear it, remember Frank Sinatra’s advice, “Cock your hat – angles are attitudes.”

The Fedora (wide brim)

Like a standard fedora, this version has the fixed crown, indented with a centre crease and pinched on both sides. But instead of the stingy brim, it has a wide, flat brim, usually 5 to 7 centimetres, that can be bent slightly upward or downward. I wear mine turned up.

This is a beautiful hat, one of my favourites. Made from soft Australian wool felt, with a nice full brim and a natural leather band, it’s ethically and sustainably handmade by Aussie hatmakers, Will & Bear. And they’re not only fair trade, they’ve also partnered with to plant 10 trees for every hat sold so I can feel slightly virtuous when I’m wearing it.

The Französin

A französin is a French alpine hat similar to the tyrolean hat, although a tyrolean is usually made from green felt and festooned with feathers or badges (see below). The French are more stylish than that, but the Französin still has the high turned brim at the back, the pointed peak, and the lofty crown.

This one is in chocolate brown felt and made not in France, but Australia, by the famous Akubra company. It does strike me as strange that the only Akubra in my collection is a French style hat.

It’s said the französin was the precursor to the homberg and I can definitely see it in the tall rounded crown and curling brim.

I bought it in a vintage store in Blackheath in Australia’s Blue Mountains. I didn’t need another hat, frankly, but as soon as I saw it I knew it had to join my hat rack. I don’t wear it as often as I should. You need to be really dressed up for a hat as elegant as this.

The Ivy Cap

The ivy cap, also known as the flat cap, is hugely popular these days. It is often confused with the newsboy (see below), which is fuller and has panels and a button. The ivy cap, on the other hand, has a low profile with a slightly rounded top that extends to the front of the hat and is sewn to the bill. Sometimes the bill sticks out a little for a different look while at other times the crown and bill are perfectly matched.

This cap was a gift from one of my daughters. She bought it in Melbourne, and it gets a lot of compliments, almost entirely from women. In fact, I think only one man has ever told me he likes it, and he said that was because it reminded him of his grandmother’s couch. Okay, sure, it looks a bit like an old lady’s upholstery, but I don’t care. It’s jaunty and kinda happy. And women really like it.

The Knit Cap

A lot of people mistakenly refer to the knit cap as a beanie, but technically a beanie is made from triangular panels of material joined by a button at the crown and seamed together around the sides. A knit cap is knitted (as the name implies) and tapered at the top.

There are various names for this kind of knitted winter hat. In Canada, they call it a tuque, from the Breton French word toque, meaning hat. In Scandinavia, where they usually add a pom-pom, they call it a top cap (Danish tophue, Norwegian topplue, Swedish toppluva), while in Britain, as I mention above, the pom-pom variety is called a bobble cap. Other names for knitted caps include woolly hat, sock hat, knit hat, poof ball hat, bonnet, sock cap, stocking cap, tossle cap, skullcap, ski hat, burglar beanie, watch cap, snookie, sugan, or chook.

This thick cable-knit rib cap by Arvust is a handsome example of the knit cap. Just don’t call it a beanie.

The Military Field Cap

The original field cap was based on the Bergmutze ski caps of Gebirgsjager, and became one of the most widely used pieces of headwear of World War 2. They were made from either olive green or field grey wool. The Bergmutze caps had a 2-buttoned band at the front that could be undone to allow ear flaps to be let down, turning it into a ‘balaclava’ like hat. This one, which I picked up in a market in Vietnam years ago is woolen, but doesn’t include a flap, although it does resemble the cotton caps worn by the Viet Cong which included the distinctive red star.

The Newsboy

The newsboy cap is the king of flat caps like the ivy, the cheesecutter, the duckbill and the ascot. A newsboy has 6 or 8-quarter panels that form into a fuller, rounder hat than those other caps. It is typically finished with a button on top and sometimes it will have a snap on the brim.

I bought this one in a quaint haberdashery in Marburg, Germany, on a freezing autumn day while my wife and I were wandering the undulated cobbled streets of that pretty little town. It is a beautiful hat and I wear it often. It’s an eight-parter with herringbone pattern, from Stetson, made under contract by Friedrich Schneider & Co, hat-makers in Oskar-Schindler Strasse, Cologne.

The Peruvian Fedora

Every visitor to Peru buys a chullo hat, those colorful knitted caps with ear flaps. But the Peruvians are also known for their bowlers and fedoras. A Peruvian fedora is made of sheep and alpaca wool and adorned with a hand-woven Andean textile band. I got mine in Cusco, Peru, and the band is actually more interesting than the hat, which is a pretty cheap knock-off of a classic fedora. Because of the vanishing art of textiles, a woven Peruvian band is a link to the traditions of the Incas, each design reflecting ancient Quechua symbols and patterns.

The Pith Helmet

This pith helmet was made by the Chop Sin Yin Leong Company in Singapore, who still make them, mainly for tourists. Up until the 1950s, they were standard wear for any Europeans traveling in the tropics, from Henry Stanley to Laurence of Arabia to Winston Churchill.

“Pith helmet” is a generic term for a hard hat made from shola pith, a dried milky-white spongey plant matter which was pressed and shaped into a hat design. There are various versions of them – the high crowned colonial, the multi-banded Wolseley pattern, the Home Service helmet, the American elephant hat, and this one, the Bombay bowler.

I can see why they were popular. This one is really light. It’s cotton-lined and quite comfortable with the leather headband buffered from the hat itself by cardboard, allowing it to stretch slightly.

Do I ever wear it? No way! It’s a symbol of European colonialism and associated with the worst excesses of the British Raj in India, the Anglo-Zulu War, the Belgian atrocities in the Congo, the Spanish in the Philippines, and the Dutch in the East Indies. It’s a curiosity piece not a fashion item.

The Pork Pie

Called the pork pie because it looks like that doughy English delicacy, this is a flat-topped oval hat with a stingy turned up brim. They first appeared in the late 19th century, but became popular after comedian Buster Keaton made it his signature look in the 1920s.

The heyday of the pork pie hat occurred during the Great Depression, but they have an enduring quality, becoming cool again in the 1940s when the black community teamed them with zoot suits; in the 1950s with The Honeymooners; in the 1960s with the Jamaican “rude boy” subculture in the UK; in the 1970s when Gene Hackman and Robert De Niro each wore one in The French Connection and Mean Streets respectively; in the 1980s when Tom Waits pulled one on; and more recently, when Walter White’s alter ego Heisenberg wore one in Breaking Bad.

This one is a bit unusual. Most pork pie hats are black, but this is a cream-coloured summer hat made entirely from paper. It’s like a cross between a pork pie and a boater. And it’s as light as a feather. And cheap. I paid eight bucks for this bad boy at a local Salvos store.

The Skullcap

The term ‘skullcap’ could refer to a number of hats — the priestly zucchetto, the African kufi, the Jewish yarmulke, the Indian topi, or the plain old watch cap. It is a brimless, rounded cap that can be made from various materials — cotton, wool, felt, kente cloth — depending on its particular style. The watch cap is usually knitted and looks a lot like a beanie. It became especially popular after World War II because of its resemblance to the caps worn by navy crew. It was a humble, everyday hat for working class men.

On the other hand, among Africans, the kufi is worn by grandfathers and other older men to symbolize their status as wise elders, religious people, or family patriarchs.

Mine is neither. It has a lightweight cotton crown, a rolled cuff, and an adjustable elastic band.  It was made in China by Yangguan and distributed by Jamont.

The Snapback

The baseball cap started off as simple five-panel cap with a long bill and an adjustable strap. Originally, they were only worn as part of baseball team uniforms, but soon fans started sporting them and they became a standard part of a team’s supporter paraphernalia, eventually becoming a fashion accessory in their own right. Jay Z claims he made the Yankees cap more famous than the Yankees.

The snapback was a further iteration as hatmakers kept the general design, including the adjustable fastener at the back, but dispensed with the baseball insignia. Nowadays, snapbacks are worn by cap connoisseurs and cool kids all over the world. Other variations include the trucker hat (like mine, which includes mesh panels at the back), and the dad hat (which has a more relaxed, oversized fit).

That said, I’m not a big wearer of the snapback. This one is by the Aussie motorcycle sales company Deus Ex Machina, branded with their Venice Beach address.

The Trapper

The trapper is an American variation on the Russian ushanka (see below), a warm cap with a fold-down ear covering. This is the genuine article, made by the legendary Stormy Kromer Company in Milwaukee. I found it in a darkened thrift store in Jackson Hole, Wyoming, in the middle of a snowstorm. It’s like God knew what a numpty I was when it comes to winter wear and had it waiting for me when I walked in.

The red plaid six-panel wool blend cap, with its flannel lining, keeps the noggin nice and warm, while the ingenious pull-down earband keeps the ears from freezing off. I wore it hiking in the snow near the Grand Tetons and fitted right in with the locals. Well, the hat did. I wasn’t fooling anyone.

The Trilby

Earlier, I included a braid hat in the style of a trilby. Here’s my woolen version. The trilby is a soft felt hat with an indented crown and a stingy brim. It derives its name from the 1897 London stage version of George du Maurier’s novel, Trilby, which was a sensation at the time. It tells the story of an innocent Irish model named Trilby O’Ferrall who is seduced, dominated and exploited by an raffish artist named Svengali. It turned out that the actor playing the rogue wore a hat of this style on stage and soon London hat sellers were promoting it as “the Trilby hat.”

I find the trilby a playful style of hat, so it’s hard to imagine it being associated with villainy and seduction, but apparently that kind of thing appealed to the men of Britain in the 1890s.

The Tyrolean

I found this lovely little Planar-Merino 100% wool tyrolean in a vintage store in Portland, Oregon. It was buried under a pile of bags and had been crushed completely out of shape, and was covered in lint and dust. I paid peanuts for it and loved it back into its former glory. Planar-Merino hats were really popular from the 1950s. I’m not sure how old this one is, but I get more compliments for this lid than any I own. Strangers have walked up to me in the street and offered to buy it from me.

Originally worn in the mountainous Tyrol region, in what is now part of Austria, Germany, Italy and Switzerland, a typical tyrolean had a crown tapering to a point and was made of green felt with a brim roughly the width of a hand. They were often finished with a cord band, feathers and badges, like this one below:

This one (above) was made by German milliners, Getes-Sonderklasse, and includes a long feather and a hat pin from the alpine village of Garmisch, a ski resort on the German-Austrian border. The pin features the Garmisch coat of arms and a flower on an ice axe. Positively Bavarian.

The Ushanka

This extraordinary piece of headwear came into my possession in the most unlikely way. I was eating lunch with friends when a woman approached us to tell us she had been clearing out her late father’s house and had come across some strange hats. She then produced this ushanka and what looked like a vintage European train conductor’s hat and asked if we would like to take them off her hands. One friend took the conductor’s hat and I claimed this baby.

Strange, I know.

A ushanka is a Russian fur cap with ear flaps, similar to what the Americans call a bomber or trapper hat. This one is pretty old and has a hard leather exterior and very soft fur trim (maybe fox) with a quilted cotton lining. The label is in Chinese and says it was made at the Xinjiang Leather & Fur Factory, which is in the far northwest of China, near Mongolia. Other than that I don’t know anything about its provenance, but I really like it. And it’s ridiculously warm.

I hope you saw a hat that interests you. Maybe it’s time for you to start a hat collection. Or to at least buy one cool hat (other than a baseball cap). Don’t worry what other people think. If you love the hat, wear it with confidence.

As designer, Philip Treacy once said, “The personality of the wearer and the hat makes the hat.”

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The views expressed are my own and do not necessarily represent the official views of Morling College or its affiliates and partners.

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7 thoughts on “My Hat Collection: my guide to male headwear

  1. I too love hats. In my town, the local bookshop owner calls me the Hat Lady! Anyway, White Collar is an American TV series (2009-2014) that I enjoyed. One of the main characters, Neil Caffery played by Matt Bonner, was asked why he always wore a black trilby. I love his response ‘Rage against the conventional.’ (I would add that the Bowler hat (I have a French one) was also worn by early settlers in Australia. My friend from the Snowies has a pic of her grandfather on a horse mustering sheep wearing a Bowler. Also, be interested in your take on Pagan Buns which my atheist friends have been baking for Easter.

    1. “Rage against the conventional” – I love it!

  2. What, no Akubra hat!?!

    1. Well, there is an Akubra hat in that list, but it’s a French design, not the typical farmer’s hat.

    2. What I meant was the classic wide-brim rabbit-felt drover’s style Akubra.

  3. Love your collection of hats! Have a small collection but my thick wavy hair sometimes makes it hard to wear a hat between haircuts, so I really only wear one to protect me from the sun in Summer.

  4. This makes me happy! I trained as a milliner in Melbourne ten years ago. This makes me want to get out my hat blocks and get to work. Maybe I’ll do it tomorrow.

    Mike, I’ve just found your blog and am thoroughly enjoying it.

    I’ve been a believer for over 20 years and have seen a lot. I am 7 years out of the church system and I don’t think I will ever go back. But I enjoy fellowship when Christians are willing to entertain it (in homes) haha!

    How I wish Christians would open up their lives for fellowship.

    The church system is a sad case.

    If only the Ekklesia inside it would come out and open their lives up for fellowship.

    Maybe then those outside would see and say, “look at how they love one another”.

    I do wonder.

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