Dress shoes can connote discomfort. They look classy, sure, but they're also stiff, like a shoe you can't dance in—which is a shame, since many dress-shoe occasions call for dancing. Cue the search ...

Sneaker-y hybrids that have no business mashing up, options that look worn out quickly, cheap-looking stuff you'd swear was plastic and not leather—we've seen some pretty ugly dress shoes.