Today's Streetwalker reminded us of a pressing question we've never managed to ask: Would you wear ankle booties? On the one hand, they're incredibly impractical and sort of ridiculous - what good is disguising your ankles if you're doing it with a massive cuff of leather or suede? They look almost medieval in their design, and they're also not that comfortable for stomping. On the other hand, they can look incredibly chic - especially since the medieval thing is actually a big influence on this season, especially if Burberry and Balenciaga are any indication. We've been gifted a very steady pair of gray heeled ankle booties - But can we actually wear them? Or is this one trend that screams "trying"?