I hated sneakers more than anything then too! I would suggest trying on a bunch of different shoes...finding the most comfortable, but fashionable
pair and then walking a little in them each day to get used to walking in a heel again. I just started to wear heels about 1 month ago and I still have a little pain after a full day in them. It just takes getting used to the angle of your toe now...I found the biggest problem to be my toe rubbing against the top of my shoes, but I am kind of used to that now.