I've worn flat caps for many years — they're comfortable, but don't keep my ears warm. So I decided to give the Rancher a try. Despite careful measuring, I ended up with one that was too small. Exchanged it for the next size up and am very pleased. It fits well, is solidly made, and much warmer on windy wintry days than my flat caps. The insulation in the top does make it a bit tall on the head (and perhaps a bit awkward looking), but its functionality has already made it a wardrobe staple.