Lacing up a pair evokes memories of roller skating’s heyday, when Boomboxes: the microphones of hip-hop’s arrival, impossibly short shorts, neon, and Prince & the Revolution records reigned supreme in roller rinks.

Cities, like people, are imperfect; they age, crack, and sometimes even crumble. Street art, like tattoos to skin, add an edge, evoke youthfulness, complexity, give historical context—like the changing of demographics and attitudes.