A gentleman's guide to the age-appropriate hat

Telegraph

11-04-2025

We've all seen the pictures of Charlie Chaplin on Wall Street, snapped in a bid to help with the war effort in 1918. The volume of the crowds is impressive enough, but the number of hats would make you think it was mandated attire. Baker boy hats, bowler hats, fedoras, trilbys, they are all there.
It's a stark contrast with today, where in the same image you'd be lucky to see a tie. We men have forgotten the delight of a good hat, but there is a rising tide of sartorialists who seek to right this particular oversight and encourage a return to this level of uniformity, perhaps if only to cover up the mullets that everyone seems to insist on today.
Brad Pitt recently made a rare misstep in the style department by donning a dubious bucket hat, normally the preserve of Gen-Z boys aping the 1990s style of their dads. It wasn't quite the thing for a man of 61, even one known for his fearless style. So how should a stylish man who's somewhat grey around temples tackle hats that are age appropriate and smart enough?
Here are the five you need to know about. But what styles are the smartest as we settle into spring events and look ahead to wedding season, regattas and various other formal goings-on?
The sleek fedora
The fedora is your classic inter-war period hat, which started being worn in the late nineteenth century. Its eponym is a fictional character Fedora Romazoff, who wears a similar style in the play Fedora, that played all over the world in the 1880s. The fedora has a little brother called the trilby, which is essentially the same but just different brim proportions.
Whilst Britain signed up to the trend owing to its wearing by Edward VIII, it was ubiquitous in America, and lent itself to everything from gangster chic to female emancipation and the sponsor hat for the American Dream in 1930s style advertisements. Hats were popular because they were an expression of social standing, the pinch at the front is for ease of removal back in the day when you'd customarily remove your hat when entering a building and greeting a woman.
There are several variants of the hat including the bash fedora, distinguishable by the straight indentation in the crown rather than the teardrop one, which you will know best as the iconic Indiana Jones hat, made by Herbert Johnson a subsidiary brand of Swaine. It can be worn all throughout the year but ranks as the least formal in this list, more appropriate for country wear than suits or separates.
Federico Anello fedora, £440, borsalino.com
The top hat
The top hat began to make an appearance in the late 17th century, with fashion norms shifting away from the knee length jacket called the justaucorps to the dashing frock coat. With it went the common use of tricorn hats and the top hat became the fashionable style for the well-heeled, whether in the city or country sports – though hunting top hats are made of firmer, weightier shells. It marks the most formal occasions, and for many years was the statesman's hat of choice when conducting official activities.
Most top hats are made from rabbit felt but you will see in vintage images that top hats were remarkably shiny and luscious, and this is because they were made with a silk plush. Alas, these are extremely rare to find as the last factory that existed which made the plush was owned by two brothers. The exact reason for the Cain-and-Abel animosity is unclear, but they fell out and one burned down the factory in spite. The machines were lost and people have tried to reverse engineer the fabric but no one has managed to replicate it, which is why the value of vintage examples are in the thousands. A top hat should only be worn with morning dress or white tie.
Top hat, £750, hilditchandkey.co.uk
The bowler hat
This distinctive fellow was conceived in 1849 by Edward Coke, the son of the first Earl of Leicester. The gamekeepers on his estate traditionally wore top hats, but as they had to ride fast through the woods between drives, they kept getting knocked off and damaged. Coke promptly went to historic hatmaker Lock & Co and asked them to come up with a hat that could deflect the low hanging branches.
It has become the headdress equivalent of the lounge suit, and should not be worn with a morning suit. It was at one point part of what city workers would wear every day, but now is reserved for the Cavalry Memorial and Black Sunday Remembrance parades in May, to be worn by officers. It should be worn only with a lounge suit; effectively the smart everyday suit you're used to seeing in formal settings.
Felt bowler hat, £99.95, hatsandcaps.co.uk
The Panama hat
The Panama actually comes from Ecuador, and traditionally comprises a tight weave of Carludovica Palmata plant straw. Its name derives from the Panama Isthmus that was used as a corridor of trade and commerce during the California gold rush. Prospectors needed a hat to protect themselves from the sun and a man named Manuel Alfaro saw an opportunity so set up a business shipping thousands of these hats to the United States. Teddy Roosevelt was pictured wearing one on a visit to the Panama Canal which increased its popularity too.
As a summer hat you'll often see it worn at sporting events such as Wimbledon, Henley and Lord's. Sometimes they will be personalised with the regimental or club colours on the ribbon. Much more appropriate than a fedora for 'summer smart' outfits, such as navy blazers with chinos or lighter-coloured suits.
Classic panama hat, £445, lockhatters.com
The Homburg
This is a handsome hat, synonymous with the distinctive silhouette of Sir Winston Churchill, that is rarely worn these days and more is the pity. That is unless you are the stylish Hollywood director Paul Feig and can pull it off. It is also known as the Eden because it was worn frequently by Prime Minister Anthony Eden, certainly the best dressed politician of all time. Prior to that it was a favourite of King Edward VII and George V, both of whom were presumably tapping into their German ancestry, as that is where the hat originates, as a style of hunting headdress. Eisenhower wore one to his inaugurations, and it was most famously worn by Michael Corleone in The Godfather.
Perhaps it's time for a return to traditional modes of dress.
Homburg hat, £44.95, cotswoldscountryhats.com
How to fit a hat properly
Hats are fitted using an extraordinary piece of apparatus called the conformateur. A miniature paper pattern of the shape of your head can be stamped by the hatter, who then cuts out the shape and sets what is called a formillion around the paper pattern. Subsequently the hat is fitted around the formillion to create the correct shape.