Ignore, for a moment, the changing winds of fashion.
Classic Hat Styles — the kinds of hats our grandfathers used to wear — have had their ups and downs in popular culture.
Sometimes they’re in, sometimes they’re out; sometimes they’re co-opted by a particular entertainer or subculture.
None of that matters much. If you want to wear a hat, wear a hat. They’re comfortable, practical, and a good way to add a touch of personal style to your outfit.
A high-quality hat is a fantastic addition to any man’s wardrobe.
That said — if you’re going to wear a hat, wear one well.
Remember, for most of the history of men’s style, hats were functional articles of clothing. They needed to look good, but they also needed to keep off sun, rain, and wind.
From those practical necessities, we get the classic style of men’s hat. Don’t get too hung up on details here, but broadly speaking a “classic” men’s hat refers to the stiff-sided, structured styles popular in the middle 20th century. Most share the same basic elements, in different angles and proportions:
Different styles of hats are usually nothing more than variations in the sizes and shapes of the brim and crown. There are a few outliers (soft flat caps, for example), but most classic hat styles fall into the stiff-sided felt family.
1. Fedora
This is what most people think about when they think of classic men’s hats. It’s such an iconic style that low-grade manufacturers will call just about anything with a brim and a fixed crown a “fedora,” regardless of accuracy.
For the purist, though, a fedora is a felt hat with pinched sides and a lengthwise crease down the crown. That gives the front a roughly wedge-like shape, though it can be molded to the wearer’s taste.
One of the big advantages of a fedora — and one of the reasons for the style’s widespread popularity — is the wide, flexible brim. Fedora brims are flat, with no constructed edge or curl, and can be bent up or down as the wearer pleases.
2. Homburg
The fedora’s dressier cousin, the homburg is your best bet for a formal business look. It has the same creased crown, but without the pinches at the sides, and the brim is stiffer and has a slightly upturned lip all the way around.
This is still the go-to dress hat of businessmen, politicians, and other well-to-do gentlemen in the western world.
3. Porkpie
A shorter style (and therefore a good one for men who are already tall), a porkpie has a flattened top without a crease down the center.
It is pinched at the sides like a fedora, creating a slightly triangular or wedge-shaped front. The brim is usually small, and turned up around the edge.
4. Bowler/Derby
The two names mean the same thing: a stiff, rounded dome of a crown with no creasing or pinching, and a short brim curled up at the sides.
Pop culture has made the bowler hat into a stuffy British icon, but its origins are working-class, and it is considered less formal than styles like the homburg and the fedora.
5. Panama Hats
Confusingly, Panama hats come from Ecuador (they were shipped to Panama to be sold to sailors and workers on the Panama Canal in the early 20th century, and the name stuck). The weaving is an art form, and true Panama hats cost hundreds or even thousands of dollars — and they’re well worth the price for men in hot, humid climates.
Most Panama hats are shaped like fedoras or triblys, but they are made from woven palm leaves or straw instead of felt. The flexible weave can be crumpled or rolled up and still retain its shape, and unlike most straw hats it can endure many soakings and dryings without distorting in shape.
Panama hats are slightly more relaxed than their felt counterparts, but that makes them ideally suited to the lightweight styles and loosened formality of tropical climates.
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