Blogging from A to Z Challenge. For those unfamiliar with the concept, it's basically about 26 posts (we don't post Sundays), preferably on a theme, blogging our way through the alphabet from A to Z. My theme this year is all about TV Tropes, celebrating random tropes with some sort of weird, odd, unusual, controversial, or taboo element that appeals to my warped sense of literary adventure.
Continuing the theme, we have Dude Looks Like a Lady (check out the page for a complete definition, but your first guess is probably pretty close to the mark). After a quick perusal of the Literature examples provided, I've gotta go with:
"The Fool in Robin Hobb's works. He even spends a few years passing as a woman, and for most of the series the Fool's exact gender is unknown, until the final book of The Tawny Man series, where it is revealed that the Fool is actually male."