The fedora reigns king of the felt hats. Fedoras have a brim that goes all the way around the crown (or top), and traditionally sport a grosgrain ribbon hat band (a silky, ribbed material). The crown can be bashed or blocked – indented and/or creased – in various styles, but the most common is a crease down the center with a pinch on both front sides. Recently popular Trilby hats are very similar to fedoras with some notable differences: a shorter crown and narrower brim that turns up in the back.
Though less formal, pork pies resemble trilbies, but with upturned rims and a circular crease on the crown, giving them a flat top. The Australian Akubra is also fedoraesque, but with a wider brim to block the sun, and usually a drawstring instead of a hat band to keep the hat from blowing away. Cowboy hats share some of these traits, but shouldn’t be confused with any style mentioned above; they tend to have a taller crown and wider brim, bashed with a crease down the middle and a pinch on either side.
Cowboys hats can be made from straw as well as felt, but is a different beast than the straw Panama hat. Similar to fedoras in brim and blocking, Panamas are actually from Ecuador, traditionally woven from palm plant straw. Boaters are also made from straw, but have a completely flat top and European origins.
Moving away from the fully brimmed, let’s focus on flat caps. Flat caps are cloth hats with a front facing brim (instead of an all around brim), and divide into two major families. Driver or ivy caps have a traditionally unbent rim (though people bend them anyway) that may be buttoned, stitched, or unconnected from the cloth top. This family includes the Gatsby or newsboy caps famously affiliated with charming street urchin. They have a floppy fit and a button on the top of the cap. Ascot caps are also driver caps, distinguished by their stiffer fabric and turtle shell look. Duckbill or pub caps are the second family and tend towards a more streamlined looked. Although similar to ivy caps, pub caps’ cloth tops are sewn directly to their bent brim, giving them a more form-fitting feel.
This may seem like awfully specific information, but there are a lot of people who take their headwear awfully seriously. The next time you roll around to your local haberdasher, maybe your newly acquired cap prowess will win you a tip of the hat.