
Someone ought to stop me. Last Saturday I took a flânerie to Kyneton, a town I’ve long intended to visit, and trawling the thrift shops for a fashionable trouvaille (as is my wont), I walked out of the Salvation Army op-shop in the main street 75 scoots lighter.
I hadn’t even been looking at it. Perusing the glass cabinet behind the counter where they keep the precious stuff, my eye had been pursuing a pair of Parisian cufflinks with interest when it fell on the lowest shelf.
Camouflaged under a heavy patina of dust and looking as battered and dinted as a busted fender was a dark grey Fedora doing everything it could to fool the unwary that it was unwearable.
My connoisseur’s eye knew better.
As a man with more hats than Zaphod Beeblebrox could ever wear, one glance told me that it was my diminutive size. And if a hat is my size, dear readers, you better believe it’s got my name written on the sweatband.
God help me. Someone put the cuffs and camisole on me quick before my mitts reach my pocket!
It was too late. I asked the lady if she would let the beast out of captivity for a moment, and she obliged. It didn’t jump up and lick my face, but then it didn’t need to. It knew it was in the hands of its new owner.
The only surprise on my side was when I turned the hat over and gave it the customary glance inside the crown. I had thought that I was dealing with a vintage Akubra, some model they don’t make anymore, and I wanted to see what creative name the marketing boys had dubbed it with.
There was a lot of gold lettering on the leather sweatband, and all legible, telling me that this hat hadn’t been worn in two or three generations. But instead of the Akubra logo I had expected to find, I saw the much rarer shield of the John B. Stetson Company U.S.A., and beneath it, the words ‘MADE IN AUSTRALIA’.
It’s hard to find an Australian-made Stetson these days. I have two others, a Springaire and a Whippet, the latter of which I was wearing when I found this baby in Kyneton.
Aussie Stetsons were made by Akubra under exclusive licence between the 1950s and 1970s, representing a synthesis of two new-world hat-making traditions. The ruggedness of the American plains and the Australian outback both demanded native brands of durable headwear suited to those environments, and the Stetson and the Akubra brands have since become synonymous with the myth of the cowboy in one country and the myth of the bushman in the other.
At the time of writing, I own about a dozen hats, including four Akubras (three of which are vintage), three vintage Stetsons, a vintage Christys’, and a number of venerable hats from British and American brands so ancient they don’t exist anymore. These chapeaux are so old that even our all-seeing oracle, Mr. Google, is ignorant about them and incapable of giving me much enlightenment as to their age and provenance.
I have rarely bought a new hat. Almost all the quinzaine of hats I have ever owned, even those that have merely spent a season with me, have had a history preceding their visitation on my head, and the older the hat is, the more I adore it.
The Stetson Centennial, for instance, gives every evidence of hardly ever being worn, and certainly not in recent decades. But after I gave it a brisk brush, a thorough treatment with B.K. Smith’s Felt Hat Care Kit, and a good steam and block over the kettle, dust and dints dropped away like the years, and the Centennial came up as nicely if it had just come out of the Myer Store for Men.

And therein lies the point: abandoned in the corner of an attic for decades, suggesting, with their mute testimony, that they may never even have seen the light of day atop some gent’s head, these antique hats have their proper lives with me. Antique as they are, they’re not curios to be displayed and never worn. They do a daily job of practical work for me, braving rain and shine as the companions of my flâneries.
I love my hats with a mad passion, and it’s fair to say that if I have one irresistible vice, it’s the acquisition of more hats, whenever and wherever I find them.
These days, I can withstand the blandishments of a beautiful dame with Olympian aloofness. But if that Lorelei were to wave a 6¾-size hat at me, I would just about debase myself in the dust at her feet in my urgent urge to acquire it. Give me more hats, O God! Let me swim in a river of rabbit fur like Scrooge McDuck in his lucre!
I don’t know where this bankrupting addiction to headgear came from, chers lecteurs, except to say that it emerged along with the passion for suits in my teenage years.
The dandy, the true-blue, pure-blood dandy, acquires a style in his youth and never renounces it. He would sooner abandon his mistress than his style. Sometimes he chooses poorly in these tender years, naïf as he is in the ways of fashion, and selects a style that does not age gracefully with him. This was the unfortunate fate of Barbey D’Aurevilly and of Robert de Montesquiou.
I think—(although I may flatter myself on this score)—that I chose more wisely than those two gents. As Richard Martin and Harold Koda say in Jocks and Nerds: Men’s Style in the Twentieth Century (1989), ‘[t]he dandy in historical regression most often directs his attention to those periods in history that provide a great wealth of æsthetic ideas.’ It would seem that for me, in my teens, when the love of suits and ties, hats and shoes overtook me as a commanding passion, that the years between roughly 1920 and 1960, between the enactment of the Eighteenth Amendment and the idiotic youthquake, I found that period of history rich in æsthetic ideas that are resonant for me.
In my soul, I’m essentially a mid-twentieth-century man, a grey flannel suit man, a silent generationer, if we take the average of those two arbitrary dates. The twenties, thirties, forties and fifties are the decades of high modernism in art and literature, which is to say, the period when the classic is at its most avant-garde. My style, as a man of letters and a man of fashion, is both classic and avant-garde, which is to say, highly modern.
The most durable thing in writing is style, and style is the single most valuable investment a writer can make with his time.
—Raymond Chandler
Having chosen the modern period as that period of history from which I draw æsthetic inspiration, and having a personal style, both literary and sartorial, that is simultaneously classic and cutting-edge, I think I have avoided the fate of those two aforementioned gentlemen. There’s still something very futuristic about the modern style, antique as it appears in our hellish period of postmodern decadence, and in a business meeting with other suited men, I can still pass, dandy that I am, as a contemporary at the forefront of creative imagination while simultaneously appearing to be a conservative standard-bearer of traditional taste.
The dandy ‘passes’ because he is the rigorous refinement of the rectitude and merciless geometry of men’s fashion: he is so ‘correct’ in his style that he shines with an uncommon éclat. Likewise, the littérateur of supreme style shines forth a unique light through the formal perfection of his manipulation of language.
In the art, the literature, the cinema of mid-century—and in its fashions—I seemed to see the diffuse image of my ‘Ideal of Personality’ as a teenager. And in the rule, the T-square, the compass and the protractor of mid-twentieth-century men’s fashion (which is to say, the suit, the tie, the shoes, the hat), I must have seen the elements of the dandy’s geometric art of correctness and precision, a supremely modern art where classical proportion meets avant-garde abstraction in the ‘putting-together’ of the individual’s vision of himself, just as the stylish writer communicates the totality of himself—his vision of the world—through the precise selection and assemblage of words.
Is it possible, dear readers, that I am the only writer who is known by his hat? The hat—more particularly, the Fedora—has become almost symbolic of me, and this seems infinitely à propos for an artist who makes his living by manipulating the abstract, cognitive tools of human language.
Hamlet claimed that he could be ‘bounded in a nutshell’ and yet call himself ‘a king of infinite space’. Similarly, that vast universe of imagination I Napoleonically command could be circled by the girth of a Fedora’s crown, say, 6¾ in size—6⅞ at most.
In thinking about this post, I scoured that sovereign empire I reign over as a despot, like Herod hunting out the boy babies, but I could not think of another writer whose image we automatically associate with the hat as a symbol of the cognitive world he commands. The closest I could come to another writer for whom the hat seems to have some stylish significance as a sartorial gesture towards literary panache is James Joyce.
As a fellow Aquarian (and thus no stranger to setting outrageous trends, literary and otherwise), Mr. Joyce had a dandistic taste for exotic headgear. Several photographs show the immense, lucid dome of Shem the Penman variously swathed in a newsboy’s flat cap, a Greek fisherman’s cap, a straw boater, and dinted, shaggy Fedoras worn with sprezzatura.
Undoubtedly, the Irish monarch of modern English letters liked a crown as much as I do. But despite this, I would hesitate to say that the first thing most people think of if they deign to bust a bissel of thought on the author of Ulysses is his hat. If anything, it’s his cane, the precious ‘ashplant’ he bequeaths to pretentious Stephen Dedalus.
So, being an ‘outdoor auteur’, a devotee of the café terrace, the park, and other undesked expanses in which it is impracticable to write, it could be that I have made the hat as much a part of my literary toolkit as my Montblanc, my Moleskine, or my manual typewriter.
I just turned 39 last month, and I bought my first hat in 1999, when I was 16 years old, so I have been wearing un beau chapeau for more than half my life—and much longer than it has been fashionable to do so.
My first hat was a black Derby of American origin—a particularly bold choice for a neophyte, and it was a bit of a false start in my hatting journey, for I recognized with the wisdom of hindsight that a Derby, or bowler hat, is better suited to a round face rather than to my narrow, delicate features.
It’s a hat that looks splendid on a fat man. Sydney Greenstreet, for instance, in The Maltese Falcon (1941), incarnates the corpulent elegance of classic British tailoring while on safari in San Francisco à la recherche du ‘black bird’, and he caps his cutaway ensemble off superbly with that signal symbol of ‘Britishness’, the black bowler hat.
Likewise, Alfred Hitchcock is everything the well-dressed London rubbernecker ought to be when he assists, at the beginning of Frenzy (1972), at the revelation of the Necktie Murderer’s latest divertissement along the Embankment. The black bowler hat completes the Master of Suspense’s funereal uniform in his brief cameo, the upward arc of the brim giving him a more than maudlin air as it contrasts with his pendulous jowls and protuberant downturned lips.
I still have my Derby, some 22 years later, and feel déchiré about the prospect of ever parting with it, even though I rarely wear it. As the most formal of my hats, it’s on active retirement, reserved for black-tie, or the races.
If you’re a gentleman, you ought to have at least one good hat that you wear regularly. A hat is the crown to any outfit you wear, and there’s rarely a man who is not improved by a good hat on his head.
And here’s a word of wisdom I can offer to the hesitant hat-virgin: If you fail to catch the hatting bug after your first acquisition, at least make sure that your sole purchase is based on what will sit well on your features; for a good hat should complete a man’s face. It should not only fit your head in girth, but in style.
With my second acquisition, made in 2000 when I was a mere gamin of 17, I was on surer footing than with the Derby. It was then that I purchased my first Fedora, a black number by Varden, a Melbourne brand that I believe has gone the way of all flesh, and which I purchased from a theatrical outfitter in Brisbane.
My goodness, did I cop some stick for wearing that hat! I was porting Fedoras years before the rappers re-popularized this piece of headgear to my generation, and you wouldn’t believe the brass-ball confidence it took to carry my crown off before the rappers made the Fedora ‘respectable’ to my millennial contemporaries.
Though the imprimatur of ‘legitimacy’ that the rappers’ gave to the Fedora subsequently made it easier for me to port my crown, it is questionable whether, in the long run, they have done the hat I loved avant la lettre any favours by their adoption of it.
Legion are now the online memes in which manboys port sweatshop ‘Fedoras’, cheaply made from synthetic patterned fabrics. And in Australia, one has to regularly swallow one’s bile at the sight of wrinkled-kneed Boomers, dressed like their grandsons in Bermuda shorts and printed T-shirts, pretending they’re at Byron with their scabrously woven sweatshop Trilbies.
Let us be clear: these cheaply-made, narrow-brimmed things clinging to the heads of Boomers and manboys are not Fedoras. A Fedora is not made in an Asian sweatshop from separate pieces of synthetic, patterned fabric machine-sewn together. It is a soft, malleable hat moulded from felted fur, such as rabbit or beaver, and as such, there is an artisanal handicraft to the creation of a Fedora.
Moreover, these imitation hats which the uninitiated partisans of YouTube cringe compilations are calling ‘Fedoras’ are, by any strict definition, no such thing. To call these ugly things ‘Trilbies’ is to give them too much dignity, but if they bear resemblance to any respectable variety of hat, the narrowness of the brim (which I suspect is more a function of the manufacturer’s miserliness than a function of fashion) brings them in line with the Trilby rather than the Fedora.
Another disservice that the rappers have done to the Fedora, and which their partisans have adopted by imitation, lies in the fundamental matter of how one wears the hat.
The problem is that the chain of succession in hat-wearing was broken by the Boomers somewhere in the mid-sixties. The abandonment of the hat, as of the suit, is one of those innumerable generational crimes for which the Boomers should be made to answer at a new Nuremberg. Contemptuous of their fathers’ style, the Boomers discarded suit and hat, and thus failed to model to their children how these items of apparel ought properly to be worn.
Consequently, when the rappers took up the Fedora a couple of generations later, they were not educated in the art of elegantly wearing it. One should never wear a Fedora straight down, with a level brim, on one’s head. Even worse, one should never wear a Fedora on the back of one’s head, like some striped-shirt hipster in Thornbury.
The Fedora, like almost all hats with a curved brim, is designed to be worn cocked forward on one’s temple, over one eye. This unwritten law was well-known to men between 1920 and 1960, in the days when a well-dressed man was not complete without his hat and fathers educated their sons in the arcanities of natural elegance by their example.
The Boomers would have had this example modelled to them by their fathers and grandfathers, but deprecating tradition, they abandoned the brimmed hat to go abroad bare-headed and bearded to the eyes, with Samson-like locks on full, flowing display.
I remember my mother said to me once, in the early years after the rage for Fedoras had been reignited by the rappers, that the hat suited me, but that she thought it rarely suited most men’s faces. I disagreed with this, as I do now, but I understood the subtler point she was making: most men who port a Fedora today don’t know how to wear it, and the Boomers who have taken up cheap imitations of the Fedora have actually forgotten how their fathers and grandfathers wore their hats.
Cock your hat—angles are atttitudes.
—Frank Sinatra
It’s not obvious that a brimmed hat, particularly a Fedora, should be worn at a distinct angle. It actually took me some time after acquiring my first Fedora to realize this fact. I would put it on in the first year and wonder why it didn’t look good.
It was Humphrey Bogart who taught me, by his inestimable example, how to port a Fedora with confident panache. While the hat, with its soft, casual elegance, eminently appropriate for most occasions, was the standard piece of all-purpose headwear for men between the wars, Mr. Bogart has become the only man one thinks of when one thinks of the Fedora.
Possibly this is due to the fact that, starting his film career in earnest as a screen gangster in the 1930’s, Mr. Bogart’s sartorial style owed a great deal to Messrs. Capone, Luciano et al., all great aficionados of the Fedora.
With the outbreak of World War II, Mr. Bogart seemed to transfer the image of the gangster to that of the crooked, though honourable, American gentleman in ambiguous circumstances—the M. Rick of Casablanca (1942), for instance. The Fedora, with its democratic adaptability, seems an appropriate hat for a man like Rick Blaine to port as he hobnobs casually with European refugees from all strata of society.
But to return to the Stetson as the best-selling brand of American Fedora, in the war years it became popular to say, quoting the company’s advertising, that one should keep information that might be valuable to the enemy ‘under your Stetson’. Mr. Bogart, representing, as no other Hollywood actor did in those years, the ‘grace under pressure’ of a kind of democratic American elegance, was perhaps the most famous wearer of a Stetson Fedora in the world at that time.
The Fedora is not a hat of the frontline, and yet it was the hat of the war years. That democratic adaptability which makes the Fedora casually elegant and appropriate for most occasions that a man might find himself in seems to fit neatly with the ambiguous image that adhered to Mr. Bogart during the war as a kind of ‘rugged gentleman’, a ‘cultivated gangster’, like glamorous M. Rick, who may be a racketeer, but who is ultimately shown to have a heart of gold.
Most days I port a Fedora of some sort, and I’m known to tout-Melbourne by my Fedoras, but my absolute favourite hat is a navy blue Homburg I acquired at an antique shop in Clunes about five years ago.
Like the Derby, I rarely wear this hat, but because, in the hierarchy of formality, the Homburg is a rung lower than the Derby, being a semi-formal hat, I wear it much more often. It’s a hat I will go months without wearing and then decide, on some random day, to wear for a ‘special occasion’—the special occasion being the occasion of wearing the hat itself.
The reason I love the Homburg so much is that it suits my features as well as the Fedora does, but adds several degrees of refinement to any outfit. I have one of the smallest heads it’s possible to hat, with a heart-shaped face and delicate, rather feminine features, so the soft yet masculine lines of the Fedora suits me well in the day-to-day. The Homburg, by contrast, has a tall but soft guttered crown and a stiff, exuberantly curved brim with a flamboyant ribbon trim, so the effect of the Fedora’s elegant lines is amplified.
The Homburg has acquired something of a reputation for stodginess, being the preferred hat of prime ministers and presidents from Eden to Eisenhower. Moreover, Tony Hancock, in his maudlin comic persona, made the lugubrious black Homburg and Astrakhan coat synonymous with postwar misery, misanthropy and miserliness in Britain.
The reputation for stuffiness is decidedly unfair, but it’s adhered so firmly to the Homburg that it’s a very uncommon chapeau to see abroad these days. Consequently, it’s a hat that requires a great deal of confidence to wear, and I would say that in our times it’s definitely the preserve of dandies like myself, because if you port a Homburg abroad, people will certainly look at you. It’s a hat that turns heads.
My Homburg is uncommonly dandistic, being a gorgeous shade of navy. The Homburg, traditionally, is either black or pearl grey, this latter being especially elegant. One often sees the grey hat paired with a black grosgrain ribbon, and it’s this variety that Michael Corleone ports in The Godfather (1972).
Though popular with gangsters in the thirties, the Homburg has less direct connection with those gents in the popular imaginary than the Fedora, and it signifies a man of affairs who is equally a man about town. It’s thus suitable for both street- and evening wear, and you can even get away with mixing a grey Homburg and black-tie if you have sufficient chutzpah to pull the combo off.
I would love to own another Homburg and am always on the lookout for one. I am a man of brims: though I have a small head and narrow features, the horizontal lines of a pencil-curled brim—not to mention the bounding arches of a Homburg’s crown—complete the bone structure of my face with an emphasis that even my customary Fedoras don’t achieve.
And here is the final tip I’ll offer about hats: When choosing a style, ask yourself to what extent the height of a crown or the width of a brim will ‘feature’ the shape of your head and your bone structure.
With a small head and delicate features, I’ve always been accused of a certain ‘prettiness’. When the lines are in proportion to my head, the exuberance and flamboyance of a brimmed hat make my head and face a site of interest.
I remember wearing my Homburg in Adelaide a few years ago and walking into a hat shop near the Central Markets. ‘The hat love you,’ the little Chinese lady behind the counter said to me. Whether she was referring to that particular hat or to the genus ‘hat’ generally, I don’t know, but certainly, having spent more than half my life wearing good hats, the confidence of a flamboyant, wide-brimmed hat says something, I think, about the strength of will, the character and cognitive capacity bounded by the crown.
I am, as I say, a ‘man of brims’. You may not be. Some men are well-served by a flat cap. The bad flat cap, however, is even more of a pestilence upon the land than the sweatshop Fedora. Be sure to get yourself a good tweed newsboy with a flexible crown attached to a short brim.
Out of curiosity, I picked up a newsboy of venerable quality from a church op-shop in Kings Cross in Sydney some years ago. You can see me sporting it in the photograph at the top of this post.

I got a lot of compliments about that cap. The flexibility of the crown was such that I could wear it with a considerable degree of beret-like jaunt, giving me the look of a Parisian apache as I wandered the streets of Melbourne with my Pentax. But despite the compliments I received, I eventually gave up the newsboy—with some lingering regret, I admit—because I had to come to terms with the fact that I am just not a ‘flat cap’ man:—I’m a man of exuberant brims, and if, as people say, there’s a touch of Gatsby about me, I’m the Gatsby of the white suit, not the newsboy cap.
The man of fashion is not complete without his hat. The dandy pur-sang is a celestial prince, like a prince of the Church. He carries the consciousness of his heavenly estate within him, and the hat is the prince’s crown. Go forth, therefore, in peace upon the earth and port thou thy hat!