Fashionable hats often feel historical. It’s not that modern society is through with inventive headgear, but we aren’t creating new hats the way we used to. In today’s hairstyle-focused world hats are stylish but vintage. Unless you wear your baseball cap to formal events, that structured piece of fabric on your head was designed decades ago and handed down through some persistent designer. It’s kind of sad people aren’t as passionate about new hats as they used to be, but you do what you can with what you have. If thinking about all the missed opportunities for new headgear gets you down, flip through the pages of history and learn the original inspirations behind the retro hats of today. There are some surprising tidbits that might come in handy if you’re a fan of Trivial Pursuit or other similarly anecdotal games. You may even find a new hat to try.
THE FLAT CAP
Next to the helmet, this style of hat is the world’s oldest cap. It originated in 1300s England to help keep the sun out of workers’ eyes as they plowed away in the fields. Since then, it’s been tweaked multiple ways to become the French beret, the American driving cap, and the famed fiddler hat of 50s biker fashion. If you’re a suspenders and leather jackets kind of guy, any of these will do you proud.
THE TOP HAT
Did you ever wonder what happened to the good old tri-cornered hat? Well, look no further. By way of the sugarloaf cap, tricorne hats rounded out their brims to become the top hat of vaudevillian and Abe Lincoln fame. First seen in 1793, this hat officially caught on mid-19th century and has been a fanciful style choice ever since.
THE PORK PIE HAT
While the men of the 1800s strutted to work in towering black top hats, the ladies went about their day in the simpler, shallower pork pie hat. A classier way to keep the sun out of your eyes than trying to control a floppy sun hat, this little number reached the height of its fame during the American Civil War. More recently, it has gained a badass reputation as the hat of choice for Breaking Bad’s Walter White.
THE PANAMA HAT
Introduced by Teddy Roosevelt after one of his trips to South America, the Panama hat is traditional Ecuadorian fare. Woven from gentle materials to make a flexible hat that lets your head breathe during the warm summer months, this is the perfect hat for summer vacations to the seaside.
Bowlers are often considered rounded cousins to the pork pie hat, but the design is more than aesthetic. Originally, the round shape was meant to protect horseback riders from hitting low hanging branches when they were out on a gallop. Later, it would become a 1920s hat for gamblers and reach international stardom as the cap of choice for Charlie Chaplin.
German at its core, this European hat was revived by King Edward VII in the 1880s and made a strong showing in 1930s England. It’s most famous outing came in the 1970s atop Al Pacino in The Godfather. Never quite popular enough to etch itself into perennial hat fashion, there are still enough niche groups to keep the homburg from fading entirely.
In the late 1890s, this iconic hat was a symbol of the women’s rights movement. That all changed in 1950 when Frank Sinatra donned it on his album cover. From that point on, fedoras were gentlemen’s hats. Even today, the style represents class and sophisticated in a way few other fashion pieces can.
The English Fedora, trilby hats made a name for themselves atop James Bond and other movie characters in the 60s and 70s. Today, it’s taken on a more casual sensibility as one of the main hats of hipster fashion. More geometric than the relaxed fedora, a trilby can be the perfect means to mixing up your classic headgear a bit.
Wearing a stylish hat makes you part of their continued history. Find which camp you fit into and start working that style into your outdoor outfits. Every fashionable man’s wardrobe features at least on good cap.
— Timothy Vest