How do I win in the fashion contests?

If she wants something sexy and elegant, only choose items that are one or the other; or both. Choose every accessory in the same manner. The hair and make up have ratings like that but for some reason it only lists those when you first acquire them. I don’t know if the person you are against is computer generated or a real one, but I win almost always. I’m often in top three on leaderboard (I spend no real $), but dont get too excited, you only get 5 diamonds for finishing in first, it should be way more, like a collection piece in my opinion.