I personally am not crazy about the idea, but I've been known to do it sometimes: while running errands or when traveling. A good rule of thumb is to make sure that you wear a top that covers your butt. I personally don't like pairing leggings with sneakers, sweats or flip-flops, anything that makes me look like I came from the gym or yoga studio. Instead, I try to pair them with casual but polished pieces, like this.
