3. Low: Pendleton Indy Hat, $58, pendleton.com
I'm feeling a dark wool fedora for winter. I know I love Pendleton's Indy Hat (I bought a tan one last year on eBay) and although the extra ounce of style is nice in Stine Goya and Rag & Bone's versions, I'm not sure they're worth three times the price.
I have been coveting the Stine Goya Legend Hat for a while though...
P.S. My girl Man Repeller looks good rocking the Pendleton Indy Hat as well