At this point, my daughter is almost 2, and she really doesn't have much interest in what she wants to wear. However, there are some things she likes to wear one day, and cries when I put it on another day, so I always pay attention to that. I don't want her to be miserable just because it looks cute. I think at whatever age she begins to show an interest in what she wears I will start to allow her choices. I'm not going to let her look like a crazy, but give her 2 or 3 options to choose from. It's great to allow kids to express themselves even at a young age, and giving them choices really helps them to develop important skills.