He’s swapped crisp button-down shirts for long-sleeve jersey polos, replaced suit trousers with roomy black cotton slacks, and kicked off derbies in favor of black Suede Puma Classic sneakers.

When it comes to men’s shorts, style experts agree: calves are in this season. So are mid-thighs, for men who dare to go there. With the dog days of summer around the corner, your legs will ...