What are your favourite pair of shoes? What are the coolest shoes you've ever seen? Do you care about shoes at all? Does someone spend all of your money on shoes? Tell us all about it... Personally I usually just where black leather boots. It's hard to find normal looking boots anymore outside of military surplus. Currently I have a pair of Sketchers boots that are as plain looking as I could find. For dress shoes I love wingtips. I have been wanting to find a nice pair of black and whites for years now. Ones like this... The coolest pair of shoes I have ever seen were ones that Ryan Stiles wore on Whose Line Is It Anyway. They were black and whites like the ones above except the white portion trailed back in the shape of a lick of flame.