My dd is 9 so this may be too young for what you are after but here is the low down. There is no uniform at her school btw. She is beautiful in my eyes but realistically pretty average in the eyes of others!
I like her to look good, but also to feel comfortable and not have to worry about not being able to do things because of what she is wearing. I also want her to have some freedom of choice about her clothes if she wants it (up until a year ago she would wear anything I chose as long as it was comfy).
She has a classic bob haircut that gets cut regularly and I am happy to pay for this. I am also happy to buy loads of clothes for her - more than she needs.
As for looking as nice as her mates...that just doesn't come into it at all. I want her to look good and feel confident - her friends can look however they look! And as for looking the best, the kids are all different, the "best" just isn't a relevant concept. Maybe this will all change in a few years. Or maybe it would be different if they had uniform. I guess it is certainly important to me for my dd to look her best rather than the best, but not to the point of being prissy & impractical! But if her clothes combinations are not what I would choose, so be it.
By Honest Pod
proud first time owner of 1 girl