Don't overthink it and get those Louboutins already. Now. The Louboutin Pigalle are a thing and rightfully so. Get the 100mm, pointy toe, nude patent kind, and you will never have to shop for a pair of heels last minute ever again. Because they will be the shoe you'll wear when everything else fails. I am an 8.5 in general, and a 9.5 in those, fyi.