Does this sound ok to wear on the first day of school?

Jeans are a good source to fall back on. It will always make you feel comfortable. I would suggest wearing a wedge, this way you will be noticed (cause of the height), and it will be comfortable. But if that is not an option I suggest wearing flats, NO FLIP FLOPS!!!! At lest not for the first day of school. Your flats should have some type of interesting detail to it like a big gold buckle. Hope this has helped