From the moment I started to care about looking cool—and I’d date this to freshman year of college, when I fell under the sway of a cadre of girls from New York whose style seemed to me unprecedentedly on-point—I have owned a pair of Chelsea boots. And for all these decades since, I don’t think there’s been a time when there wasn’t a pair in my my closet. These days, they seem less about cool (likely because, at 51, I am less about cool) than about supreme versatility: they can come off anywhere from classic to edgy, and are just so very walkable. My current favorites are Blundstones (see first pair below) because they’re endlessly comfortable, the treads make them good for when there’s snow and ice, and the price is right. But I’d happily say yes to every pair you see here too.