First of all, cut the evening shoes down to one formal, for both nights, and one nice heel for more casual nights. Then you only have 2 sets of high heels to worry about. I pack flat shoes, like flat sandals and sneakers and husbands dress shoes flat on bottom of suitcase. Then I fill with clothes. I put nicer shoes on the side with the heels away from the clothes. Then you can put other flip flops, etc. across the top of the bag before you zip.