On the first day of school, you need clothing and accessories that you know you won't fuss with and won't break or stretch halfway through the day. Bring the cardigan just in case it gets cold in the classrooms and the arch supports are much needed when wearing flats.
The blazer and the heels polish up the grungy-ness of the look while the earrings add a playfulness.
Get into fall with brown accessories. The heels are small which are more comfortable than sky-high heels but make the look more put together.
If you're looking for a more in-the-now look, then pair a sheer maxi skirt with sky-high wedges, a roomy tote bag, and turquoise nail polish.