Portland Outdoor Store
Credit: Anthony Pidgeon / Getty Images

The Portland Outdoor Store is a rarity, a legitimate, old-timey frontier outfitter that's also bracingly modern. It's been a city landmark since 1914 and today you'll find brands like Stetson, Filson, Levi's, and Barbour on the long shelves. Perfectly worn-in vintage jean jackets are a particular strong area, as are cowboy shirts that range from plain spoken to flashy.