The Perpetually Misunderstood Panama Hat

Man wearing a panama hat
Image credit: Kevin Mueller on Unsplash

Putting on a hat before leaving the house can these days feel like just about the riskiest move you can make, sartorially speaking. In most cases, you might well be alright if the headgear in question is a baseball cap or maybe a bucket hat, though even then there are no guarantees. To cover one’s cranium seems inevitably to suggest you’re hiding something: a bad haircut, a receding hairline, some dodgy intentions, or maybe even an identity that’s best kept secret. And when we’re talking about a choice that’s a little bit more out there — like a beret, a fedora, a flat cap even — forget it. Unless you’re a supremely assured dresser, any hat that seems at all outré may as well have a ‘KICK ME’ sign pinned to the crown.

There’s also a great deal of uncertainty about hats in general, no doubt because of a fear that asking too many questions might suggest we’re thinking about wearing them, at which point we’re right back to the mess described moments ago. As a result, there is a lot that remains unclear. For instance: Is this a trilby or a fedora? Did JFK really put an end to men wearing hats? Will a beret make me look more like a military dictator or an exchange student à Paris? Has anyone in real life actually ever worn a pork pie?

It’s a pity, really, because there are good reasons why you, like me, might continue to want to wear fancy hats. Despite everything implied by present-day dressing norms, formal headwear feels somehow inescapably stylish, practical, and like they would be a hoot to put on every now and then. They play into our nostalgia about a forgotten (and no doubt imaginary) world in which all men dressed well; a world we hark back to every time we have the impulse to try on a homburg or a bowler hat only to be reminded that these are tifters that are all sadly extinct in the present day. 

Vintage man wearing a Panama hat
Image credit: State Library of New South Wales / No known copyright restrictions

Just about the only bit of formal headgear you could get away with wearing these days is the Panama hat, though it is itself not exempt from a measure of mockery you’ll have come to expect. Josh Sims in Icons of Men’s Style, for instance, opens his entry on the Panama hat by describing it as being a longtime favourite of ‘ageing golf pros, dapper horse-racing pundits and the retired middle class’. Not exactly the most ringing of endorsements. 

There is also a good helping of on-brand confusion to be found on the subject. The name, for example, is inaccurate. These hats don’t come from Panama and never have done. Instead, they hail from Ecuador where locals have been making hats woven out of fine toquilla straw for hundreds of years. 

There is some further uncertainty regarding how exactly this particular hat, known in its true country of origin as the sombrero de paja toquilla, got the misnomer ‘Panama hat’. One theory has it that once the style had become popular internationally, they were imported to Europe via Panama. Another attributes the coinage to widely disseminated photographs of President Theodore Roosevelt’s 1906 visit to the Panama Canal during its construction. He was, of course, wearing none other than the woefully mislabeled hat in question.

President Theodore Roosevelt wearing a Panama hat
President Theodore Roosevelt causing a world of future confusion by wearing a certain hat style at the Panama Canal
Image credit: Library of Congress / Public domain

In truth, as per the New York Times:

‘The term “Panama hat” has been in use since at least the 1830s, and came about because the hats were often sold in trading posts on the Isthmus of Panama, which was a shipping crossroads long before the canal was built. The name was popularized during the California gold rush, when tens of thousands of prospectors passed through Panama on their way to the diggings, many of them picking up a hat along the way.’

Roosevelt and other high-profile fans certainly helped popularise both the name and the style of the Panama hat. In 1855, by which point more than a quarter of a million hats a year were being sold out of Panama, a Frenchman who had been resident in the region gifted a particularly fine example to Napoleon III, who liked it enough to wear it everywhere he went. Not to be outdone, King Edward VII duly instructed a hatter to spare no expense in finding him the finest Panama money could buy. Many others followed suit and in time the style achieved a sense of urbanity thanks to famous wearers like Winston Churchill, Harry Truman, J.P. Morgan, Al Capone, Salvador Dalí, Humphrey Bogart, Gary Cooper, and Frank Sinatra.

Grace Kelly and Frank Sinatra wearing a Panama hat
Frank Sinatra wearing a darker-hued version of the Panama hat next to Grace Kelly in High Society (1954)
Image credit: Tullio Saba / Public domain

True aficionados have long been willing to spend extravagant amounts of money in pursuit of the perfect Panama. A ‘Talk of the Town’ piece from The New Yorker in July 1930 mentions a $1 000 dollar number on sale at Dobbs department store, a sum that at the time could have bought you a brand new car with cash to spare. Nothing much has changed in the interim apart from a level of price inflation that means that the finest examples can fetch tens of thousands of dollars today.

The vast majority of contemporary Panama hats are woven in the town of Cuenca high up in the Andes. In the mid-nineteenth century, once the style had proven popular abroad, the local government prompted residents to turn their collective hands to hat weaving. This led to a commercial level of production that today means most of the Panamas found in hat shops and department stores around the world come from Cuenca.

The aficionado’s choice, on the other hand, invariably hails from Montecristi and its surrounds where hat-making has remained a cottage industry and something of a fine art. It’s here that for generations weavers have been gathering and prepping their own straw before meticulously crafting hats in a herringbone style known as ‘liso’. To quote Sims again, albeit this time in a more complimentary but equally evocative vein:

‘Each hat is handmade — no two are alike — and takes months of work by one of a dying band of artisans, who prefer to weave without bright light and ideally on a cloudy day as this makes it easier to see the fibres. On the very best examples, the edges are woven back into the brim; on lesser versions the brims are trimmed and sewn. After the hat is made it is pummelled — a craft in itself — to create regularity and suppleness, washed in rainwater, hand-ironed to bring it back to shape and, finally, trimmed. Panamas are naturally pale cream, though darker fires are sometimes worked into the design for interest’s sake, or an entire hat is bleached white using sulphur from the region’s volcanoes.’

A group of unfinished Panama hats
Image credit: Alexander Schimmeck on Unsplash

He goes on to call the Panama hat ‘the king of summer headwear’. It’s hard to disagree. Every time I dream about holidaying in an exotic tropical locale or catch sight of a picture of some midcentury celeb doing the same, I am tempted to buy one. To this end, I have eagerly clicked on any number of articles declaring a particular Panama hat the best in the world and carefully studied the advice of any number of buyer guides over the years. And yet I have never pulled the trigger.

My lack of action has everything to do with the miasma of taboo and uncertainty surrounding hats mentioned above. But who knows, maybe next summer I’ll take the plunge. That way I can finally embrace the ageing, middle-class golf pro I’ve secretly always wanted to be.