Once upon a time, no decent gentleman would show himself on the streets without a hat.
The rebellious 1960s changed all that, and by and large hats went the way of the dodo. Today, hats have experienced a resurgence in popularity and the streets of Brooklyn, Portland, San Francisco and other natural hipster habitats are teeming with men sporting headgear. But fear not – you don’t need ironic facial hair or an obsession with craft beer to wear a chapeau and look great doing it.
If you’re in the market for a hat, you’ll need more than a glancing familiarity with the classic styles. The fedora was the classic men’s hat worn from the 1920s to the 1950s until JFK, a style-setter among men, began appearing in public hatless. The classic fedora is creased down the length of the crown, and then pinched near the front on both sides. The brim, sturdy but flexible, can be snapped up or down in the back or front, allowing the wearer to achieve the desired shape. The homburg, the fedora’s more formal cousin, is similarly shaped but has a stiffer brim and an upturned lip all the way around.
The trilby saw widespread popularity in the early 1960s, when a lower head clearance in American cars made it impractical to wear a topper with a high crown, particularly for the taller gentleman. The trilby has a shorter and narrower brim that is angled down at the front and turned up in the back.
The amusingly named pork pie has a narrow, turned up brim and a flat top with a circular indentation. Popular with the classic jazz club hipster (the original hipster, as opposed to today’s fixed-gear bike riders), this style was most recently and famously worn by the character of Walter White (in his “Heisenberg” persona) in the series Breaking Bad.
The Panama hat is the classic of tropical wear. Originating in Ecuador and made of straw, the style is similar to a trilby in terms of brim, but more like the classic fedora in proportion. The hats are traditionally made from the plaited leaves of the Carludovica palmata, a palm-like plant.
The most expensive of these hats, known as Montecristis (after the town in Ecuador where they are made), can have as many as 1600-2500 weaves per square inch. The town’s Montecristi Foundation has established a grading system based on measurements of the horizontal and vertical rows of weave per inch. A “superfino” Panama is said to be able to hold water and pass through a wedding ring when rolled.
The boater, reminiscent of turn-of-the century English schoolboys punting in striped jackets, is a formal summer hat made of stiff straw. The brim is inflexible and the top flat, with the crown circled by a band of grosgrain ribbon. Also popular among preppy Northeasterners, this hat is best suited to the dandiest of dandies.
For more information, please read:
A Guide to Men’s Hat Styles | Articles of Style