The classic Northwestern outfitter Filson have been making quality headwear for over a hundred years so you can trust that they're doing it right. They make some classic full brim hats that not everyone can pull off, but these days they're also doing some really exciting collaborations. Take for instance their Classic Cap (pictured above) that's been re-imagined with help from Levi's: water repellent materials on the exterior keep out the rain while the blanket lining inside will keep your dome nice and toasty.
Like I said, not everyone can pull off a full brim hat without looking silly (especially in urban settings) but if you think you've got it under control the Tin Cloth Packer Hat
is great choice.
Channel your inner Elmer Fudd in the Double Mackinaw Cap
. While this option might not be the best for wet days it'll certainly keep your head as warm as possible with some seriously thick wool and real sheepskin on the earflaps. -Bob