If you're going to crash summer-shares this season, your look should exude free-spiritedness -- otherwise, your upstanding appearance'll make people think you actually intend to chip in cash. For a bag steeped in a culture of feckless nomadism, try the Hobo, from Barking Irons.
Like Barking's clothing line, these just-released bags draw influence from New York's grimy 19th Century underworld -- specifically the makeshift duffles carried by itinerants who'd descend on The Bowery to blow their money on wine, women, and tickets to see the Cold War Kids. The lining's soft poplin, but the canvas exterior's tough enough to throw out of a 2nd floor window, then break your fall after you're thrown out of a 2nd floor window. In a nod to modernity, there's also a side zipper pocket, where you can stash electronic devices, or dented cans of beans.
As for artistry, the front's emblazoned with BI's signature crossed pistols, and a threat once issued by a gangsterish politician encouraging the above itinerants to vote: "[We will dirk] Every mother's son of you". And like you plan to, clever hobos hopped on the next train out of town.