Portland, ME
Best brands: 3sixteen, Portland Dry Goods Private Label, Reigning Champ 

Maine's quest to be America's home of the moccasin is only trumped by its ability to keep them lobsters rolling in for us all. But those moccasins can pretty much all be found at Portland Dry Goods, along with some immensely complementary menswear from brands like 3sixteen and PDG's in-house label. If you're a fan of classic gear that stands up to the elements and doesn't make you look like a walking blog post from 2011, then this is your go-to spot.