I wear leggings with a cute top or dresses. I don't wear jeans to work but that's just because I prefer leggings. My style is definitely casual. You'd never catch me wearing a pantsuit, for instance. Not that I would anyway because I think suits are unflattering on most women. I don't dress up because of my grade level. That's partly why I keep my dress simple. I'm running around and on the floor a lot, getting glue and glitter on everything, etc. So for my grade level it works. Other female coworkers dress similar to me, no matter what grade level. The male teachers seem to wear whatever lol. OP, just adjust your outfits based on grade level and atmosphere of the school. I'd suggest that you don't over-dress and wear heavy slacks and a blazer everyday if you work with the younger grades. But that's just me. Jeans and 1 pair of black pants + five cute tops and you should be set. Just rotate them and it will be un-noticeable. They want you to look neat and nice, but if you present yourself with a positive attitude your clothing will hardly matter. You are there to listen and absorb as much as you can. Don't worry about being "stylish"