How to Run in Heels

On his heel of choice: Initially, I wanted to run in full-on stilettos. When I was preparing for the event, I wore a pair of black, five-inch Jessica Simpson pumps, but after a few test runs the heel proved to be too thin and dangerous. Ultimately, I picked a classic—a pair of size 11 black distressed-leather Lita by Jeffrey Campbell. They have a thick enough five-inch heel that won't break your ankle and a really solid toe-box so that your feet will stay in one piece. They're actually a lace-up bootie, so they won't fall off when your feet get a little sweaty—as perfect as heels can be for running.

On training in his new kicks: I only trained a little bit, because running in high heels is in NO WAY good for your feet. I wanted to make sure that I wouldn't break my ankle, but past that I didn't do any serious training. No one should regularly run in high heels, and high heels should only be worn in moderation; I don't want any podiatrists coming after me, so I want to be pretty clear about that.