Up until the late ’50s, a hat was an integral part of a man’s wardrobe, but the ’60s through the well-made hat into a tailspin with the floppy leather thing-a-ma-bob and the beanie.  The informality and the influence of sports has essentially reduced hat wearing to beanies and baseball caps.  For much of 19th century America and the UK, the hat symbolised not only economic class but also could distinguish ethnic groups in the urban context.  Martin Scorsese brings this out so richly in his epic film Gangs of New York, which in fact could be an ode to the Age of Hats.

For much of the maligning of the hipster, the combination of tattoos, tailored clothes and the beard/moustache question brough back a reconsideration of the proper hat and, to be frank, a bearded and walrus-moustached face looks better framed with a nice bowler.  A number of designers have picked up on the hat as an accessory, primarily driven by the success of Mad Men, but with a twist to more “eccentric” shapes and colours.

This slideshow requires JavaScript.

The old hat is now the new hat, but let’s take a quick look at all of the forms of men’s hat and the best way to wear them.

The Fedora

The Fedora

For most men, the fedora is the most familiar of hats.  Made popular by the series Mad Men, the hat is typically creased lengthwise down the crown and “pinched” near the front on both sides.  Fedoras can also be creased with teardrop crowns, diamond crowns, center dents, and others, and the positioning of pinches can vary.  The brim is usually wide and can be left “raw edged”, finished with a sewn overwelt or underwelt, or bound with a trim-ribbon.  The brim is usually folded down in the front and up in the back.  You can give the fedora a bit of young and careless look by folding the entire brim up, making you look slightly London ’70s.

The term fedora was in use as early as 1891. Its popularity soared, and eventually it eclipsed the similar-looking homburg, becoming associated with the gangster look.  Quality fedoras are made of felt and come in a variety of colours but should generally be in a very narrow range of black, grey and tan.

The fedora is a great all-around hat but excels in cooler temps as well as being excellent rain-protection.  Properly treated, a fedora hat will last for several generations.  Personally, I have a French-made fedora from 1939 that always looks good going out.


The Homburg

Homburg hat

The classic Homburg

The Homburg is similar to the fedora but has narrower brim that “snaps up” on the sides as opposed to the front and/or back.  The crown is gutter-dented on top but with less pronounced side-dents.  The Homburg is also stiffer, giving it a more formal appearance than the fedora.  Popularized by Edward VII after he visited Bad Homburg in HesseGermany, King Edward VII was exacting and expert in all sartorial matters and promoted this style excessively. He was therefore flattered when his hat style was copied; at times he insisted on being copied.

The Homburg gained considerable popularity in the 1930s and was called ‘the Eden’ on Savile Row due to Anthony Eden promoting the hat.  Eisenhower apparently wore one to his inauguration in 1953.  In America, the hat came to be associated with gangsters in a similar way to the fedora.  Much like in the Gangs of New York, organised crime diversified its head gear for the purpose of identity.  Al Pacino famously wore a light grey homburg in the godfather.

Recently, I purchased a beautiful brown homburg from Lock & Co. hatters.  A hat I hope to pass on to somebody, somewhere…


The Trilby

The troublesome trilby

The troublesome trilby

Ahhh….the trilby.  As a hat, this sits where hats don’t want to be.  From a shape perspective, it’s a fedora with a very narrow brim which are “snapped” up and down.  The trilby originated from the stage adaptation of George du Maurier‘s 1894 novel Trilby, of which a version of the hat was worn in the first production.  Traditionally made of rabbit hair felt, the material of its making now goes from straw to denim.  It looks a little bit like a Tyrol hat.

The difficulty I have with a trilby hat is that no one looks good in one.  Maybe you can get away with a straw one (as pictured) in a hot clime, but the short brim never seems to work.  I own 2 trilbys (from Rag & Bone and Lock & Co.) and struggle to wear them out.  I look like an old man trying to be a 20-year old at Daytona Beach for Spring Break.  Or an aging rocker who has never had a hit song.

Ok.  I could donate these to the Salvos, but then I would essentially be passing along sin.  Let’s top this now.  Bin them.


The Panama Hat

Panama Hat

The Panama Hat – a classic for the international traveler (or our man in Havana).

Palm trees above.  Havan cigar smoke.  Beautiful women and men in bright colours.  For me, this is the context of the Panama hat.  A traditional brimmed straw brimmed hat, it has its origins in 17th c. Ecuador.  Traditionally, Panama hats were made from the plaited leaves of the Carludovica palmata plant, known locally as the toquilla palm or jipijapa palm.

Panama hats are light-colored, lightweight, and breathable, and often worn as accessories to summer-weight suits, such as those made of linen or silk. Beginning around the turn of the 20th century, panamas began to be associated with the seaside and tropical locales and became popular with the ex-pat communities in Latin and South America.  In 6 Dec 2012, the art of weaving the traditional Ecuadorian toquilla hat was added to the UNESCO Intangible Cultural Heritage Lists.  Which means that the tradition will be preserved for a long time.

One of my favourite aspects of the Panama is that for warm weather, it can hop between refined, worn with a crisp white linen suit or get beat-up a bit and worn with more casual attire.  From a traveling standpoint, a good Panama can be rolled up and stored in a box.  The two main processes in the creation of a Panama hat are weaving and blocking.  The rarest and most expensive 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.  A “superfino” Panama hat can hold water, and when rolled for storage, can pass through a wedding ring.  In Italy, Borsalino makes a very fine Panama hat.


The Boater

The Straw Boater in Penn colours

The Straw Boater in Penn colours

As the Thames or the Seine languidly wind their ways down the greatest cities in the world in the heat of summer, young gentleman sip Pimm’s or champagne while wearing linen and seersucker suits of extraordinary lightness, topped by the most perfect of summer hats – The Boater.  It is normally made of stiff sennit straw and has a stiff flat crown and brim, typically with a solid or striped grosgrain ribbon around the crown often representing the school of the wearer. They were supposedly worn by FBI agents as a sort of unofficial uniform in the pre-war years (This cannot be confirmed but makes for a good story). Nowadays they are rarely seen except at sailing or rowing events or as part of old-fashioned school uniform, such as at Harrow School.  In AustraliaNew Zealand and South Africa the boater is still a common part of the school uniform in many boys schools.

Being made of straw, the boater was and is generally regarded as a warm-weather hat. In the days when all men wore hats when out of doors, “Straw Hat Day”, the day when men switched from wearing their winter hats to their summer hats, was seen as a sign of the beginning of summer. The exact date of Straw Hat Day might vary slightly from place to place. For example, at the University of Pennsylvania, it was the second Saturday in May.

The boater is a fairly formal hat, equivalent in formality to the Homburg, and so is correctly worn either in its original setting with a blazer, or in the same situations as a Homburg, such as a smart lounge suit, or with black tie. John Jacob Astor IV was known for wearing such hats. The silent film comedian Harold Lloyd used the boater, along with horn-rimmed glasses, as his trademark outfit.

The Bowler Hat

Charles Thyrwitt Bowler Hatt

The Charles Thyrwitt Bowler Hat

In our modern day, the bowler hat seems to have been relegated to the fashion wardrobes of teenage girls who want to play a little bit of Annie Hall avant-garde, but back in the day, the bowler was the only hat a proper Englishman would wear to work at his bank.  And again, their is a certain irony in 19th century workwear that the a dusty, ragged bowler brings to the formality of the bowler.  The bowler is a very hard hat with a round crown and narrow, side-curved brim.  Invented in 1849 for Edward Coke, the 2nd Earl of Leicester, Thomas and William Bowler contracted Lock & Co. Hatters to make the hats to protect the heads of the Earl’s gameskeepers.  Eventually, it became the headgear of English civil servants and bankers and eventually the American worker.

The bowler is an iconic hat representing a love British tradition and it seems that its popularity has spread to Africa and Bolivia, where it is a traditional head dress worn by women of the Quechua and Aymara Indian tribes.  Personally, I don’t own a single bowler but I think there may come a time and place where I need one…Maybe when there is a run on the bank.




The Flat Cap or Newsboy Cap

flat cap tweed

The flat cap

The flat cap is “the” cap of the late 19th and early 20th century.  Worn by almost everyone in the British Isles and Ireland, the flat cap is variously known as Paddy caplongshoreman’s capscally capWigens capivy capgolf capdriving capJeff cap, or in Scotland, bunnet, or in Wales, Dai cap, or in New Zealand, cheese-cutter (my favourite).  The cap is generally made from tweed with a stiff brim overhung by the top.

The style can be traced back to the 14th century to Northern England and the south of Italy. When English and Irish immigrants went to the United States, they took the flat cap with them.  A 1571 Act of Parliament to stimulate domestic wool consumption and general trade decreed that on Sundays and holidays, all males over 6 years of age, except for the nobility and “persons of degree”, were to wear woollen caps on pain of a fine of three farthings (3/4 (pence) per day. The Bill was not repealed until 1597, though by this time, the flat cap had become firmly entrenched as a recognised mark of a non-noble subject, such as a burgher, a tradesman or an apprentice. The style gave rise to the Tudor bonnet still used in some styles of academic dress.

In the 19th and early 20th centuries, when men predominantly wore some form of headgear, flat caps were commonly worn throughout Britain and Ireland. Versions in finer cloth were also considered to be suitable casual countryside wear for upper-class English men (hence the contemporary alternative name golf cap). Flat caps were worn by fashionable young men in the 1920s. Boys of all classes in the United Kingdom wore flat caps during this period.

In the United States the caps were worn from the 1890s. The cap grew in popularity at the turn of the 20th century and were at the time standard boys’ wear. They were worn to school, for casual wear, and with suits. Flats caps were almost always worn with knicker suits in the 1910s and 20s. Both flat caps and knickers declined in popularity during the 1930s.

I have approximately 8 of these, all made of Donegal tweed.  As far as I am concerned, if your flat cap isn’t made in Ireland or Scotland, you might as well where a baseball cap…

The Newsboy Cap

newsboy cap

The newsboy

The newsboy cap is a variation of the flat cap made from panels of cloth held together by a button on the top.  It is usually baggier and can have the look of a beret.







The Top Hat

The Top Hat and case

The Top Hat and case

I end my discussions of hats with the Top Hat.  Many have seen the top hat in media but few have had the lucky occasion to wear one.  Unless you are at Ascot, evening suits or tails are generally worn without headgear.  The top hat is a difficult one as it is at the height of formality and, unlike other hat styles, a working class version has never really existed.  For much satire in the 19th century, the top hat symbolised the “fat cat” and the lesser aspects of capitalism.  Originally, they phased out the tricorn from normal aristocratic wear.

Confined to the role of as a keeper of magic rabbits, the top hat requires its own specialised case for storage.  These were often complicated and expensive leather contraptions that were extremely large.  The top hat is often made of beaver fur felt (another name for it is beaver hat) in contrast to other molded hats that were primarily made of rabbit fur felt.  Gradually the beaver fur was replaced by silk plush, and even tops of oilcloth to protect the wearer in foul weather.

Nowadays, the top hat is an anachronism, reserved for royalty and weddings, never to be worn again in the exaggerated proportions of Daniel Day Lewis’ Bill ‘The Butcher’ Cutting.


As far as hats go it is time to sign off but I leave with the idea that a revival of this noble accessory would be positive for the sartorial cause.  BTW, here is a good Pinterest collection of hats from Hats Off and a collection of videos about hats, especially the making of a Barbisio.