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The best casual shoes for men make dressing for almost any situation – in almost any season – a total surprise. To be clear, when we say “casual shoes” we’re using the term very liberally (that is, as a general term that includes everything from suede Chelsea boots to high-end luxury sneakers). Basically, if you’re not wearing it to tear up a wedding dance floor or break your ankles on the playground, you’ll find a copy of it listed here. Grab a daytime drink in the park on sunny weekend afternoons, rock your nephew’s backyard piano party, and dress up on the IRL date you lined up months ago in an ominous wave of unbridled optimism.