This chapter examines the contrast between street vending and city regulatory responses in Vancouver, Canada during two time periods—the 1970s and the 2010s. The comparison of “hippy” vending in the 1970s and “hip” food carts and trucks four decades later illustrates the contradictory impulses that shape regulation of commercial activity on city streets. First, there is a process of “formalization” that seeks to tame the informality and messiness of street vending through new rules, standards and regulations. But by the 2010s, a second, contradictory, impulse appears: an embrace of informality reflecting new ideas about “vital” city streets and identifying street vending, in the form of food trucks and carts, as “hip.” But the apparent embrace of the informal has unfolded through highly formalized procedures, and the vitality associated with vending in Vancouver is acceptable precisely because it has been (re)introduced in a highly formalized, regulated form.