At first I started out in fairly safe places like shoe stores... I'd wear my flip flops in and spend an hour trying on different shoes. You will always draw attention, because a guy sitting down on the womens section to try them always does. I always found it best to go to a "self-serve" type shoe store first, then move on the department stores where you have to ask for sizes. However, the department stores always spark the greatest converstions, and the staff usually jumps in and points me to some great finds, especially since I wear a size 11 and they are a bit rare at times. I also like wearing heels to great safe places like hip hair salons to get my hair cut. The girls always go gaga over a man in heels... I think they as just more open minded, for some reason. I trully have had never had a really negative experience, just some funny looks!