Head into spring with a new hobo! The Pieced Out Hobo ($398) from Hayden-Harnett won't disappoint. It's made of a bright raspberry-dyed goat leather which only gets more soft and supple as it ages, and it's got size on its side. It's large enough to fit your iPad, but not so huge that you'll be digging through it for fifteen minutes before you finally find your keys.
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