This isn't your ideal penny loafer. Sure, it's cognac and has the square toe and the little money-slit on top. But check out that heel. Great legs would pull this one off in a sexy- cinch; your legs will definitely be a standout. I would pair this with a haute, black, designer short- suit for work. The shorts would have to be super-short and you would want the blazer to be tucked at the waist. Ouch! I can feel it!