I’m bald, and my father was a hat hobbyist, so I come by my hat interest biologically. Furthermore, I grew up in the northern midwest — I know about cold ears.
These two wool-plus hats from Tilley are the best winter headgear I know for wear-around use.
The “Winter Hat” is a tweed marvel, with short sloping brim all around, fold-down ear flaps, and a fold-down forehead warmer (a great comfort against a chill headwind, but invisible to others, being hidden behind the brim). The ear flaps are slightly cupped around the ear for further wind protection. The wool is teflon-treated, so rain and snow pretty much bounce off. The hat can be folded into a jacket pocket, yet retains its shape perfectly. In two varieties of tweed, plus black, it’s a surprisingly handsome hat—“friendly,” Brian Eno called it. People call out: “Nice hat!”
The “Winter Cap” looks like your basic New England wool deer hunter’s cap, with big baseball-cap brim and ear flaps. But it has the Tilley augmentations—forehead flap, teflon treatment, excellent construction. I love it under a hood in cold precipitation—keeps my glasses dry and clear. Black or red; get the red.