The best casual shoes for men make dressing for almost any situation a total snap. To be clear, when we say “casual shoes,” we’re using the term liberally (i.e. as a catchall phrase that encompasses everything from suede Chelsea boots to swanky high-top trainers). Basically, if you wouldn’t wear them to tear up a wedding dance floor or break ankles on the court, you’ll find a version of them included here. Wear ’em day-drinking in the park on a surprisingly mild winter afternoon, wear ’em to your snotty nephew’s backyard piano recital, wear ‘em on that IRL date you lined up months ago in an ill-fated burst of unbridled optimism. But wear ’em you should.
What, you might ask, makes all these shoes so worthy of your hard-earned pounds? An unparalleled ability to elevate your cold-weather style, for one. A certain seasonally appropriate versatility, for another. So forget that time-honoured debate over whether you should build your outfit from the top down or bottom up—once you throw on a pair of these bad boys, it won’t matter whether you’re rocking shorts or sweats. From classic trainers to chunky loafers and every wild-style permutation in between, consider this your not-so-definitive guide to the very best casual shoes for men on the market right now.