Garnette Cadogan, an old-school flâneur and essayist, wrote a fantastic piece describing the differences between walking while black in his home county of Jamaica, compared to New Orleans and New York City in the US.
As he notes, he developed his habit of late-night strolling as a tween in Jamaica of the 1980s, when the streets were wracked with violence, and you could "get killed if a political henchman thought you came from the wrong neighborhood, or even if you wore the wrong color". Yet he found it even more destabilizing to walk in US cities, where he was the subject to endless suspicion from other passersby and the police. He winds up finding it difficult to achieve precisely what city-walking is supposed to permit: That feeling of losing yourself in your surroundings.
There's so much great detail and nuanced observation in this piece, you should go read it all; but this passage near the end struck me as particularly deft. Cadogan talks about the randomness -- the capriciousness -- with which police or other people would suddenly threaten him in US cities, and how that's particularly psychologically wearing:
I realized that what I least liked about walking in New York City wasn’t merely having to learn new rules of navigation and socialization—every city has its own. It was the arbitrariness of the circumstances that required them, an arbitrariness that made me feel like a child again, that infantilized me. When we first learn to walk, the world around us threatens to crash into us.Read the rest