Emma Watson
Only Emma Watson could pull this look off flawlessly. She’s taken plenty of fashion risks before, but always keeps it tasteful, which is why she’s constantly a go-to for outfit ideas. Even though we’re not quite sure we’re ready to start throwing our dresses over pants like it’s 2002 again, we applaud Emma’s bold choice — and shudder to think what could have happened if that same dress ended up in the hands of, say, Erin Wasson.