heya! i don’t think trying to wear heels to school is stupid. of course, school is a serious place and we wouldn’t want to get into any trouble with our appearance. but for heels, i don’t see anything wrong with it! for a start, try simple basic heels. i can suggest a pair of kitten heels/pumps for comfort! or a pair of low wedges will be great too!
for example, a solid v-neck tshirt, skinny jeans, and a pair of heels. (try floral prints if you want some spring fashion, heeled oxfords for a modern vintage look, or wear a grey kitten pair with white tshirt and basic jeans).
another example, a basic tank top, a cute cardigan, jeans and a pair of pumps. (this pair of slingbacks can have a simple cute bow on the front, or a leopard prints pair will be great too! or try a pair of solid color simple strappy sandals!)
try not to go for sky-high heels because walking around for classes and with the crowd rushing for lunch might just end up with you falling down! once you have gotten used to wearing heels, you can slowly move on to the higher ones and remember, stick to the more simple designs for school! 
