It can be amusing making outfits for sims. They will like the oddest things and hate the pretty stuff that I like! It does help to have charisma up so you can get friendly with them quicker. Discover their traits and favorites helps too. Sometimes it can be a pain trying to make friends if they need to go off to work though. Just click on the option when the picture option comes up. You don't even have to take a picture of the shoes so don't worry about lining up the shots. Taking the picture is what counts for the portfolio not what is in the picture. Silly sims.