Story by Caitlin Agnew. Jacket ($49.50, at Dynamite), inspired by a certain Clueless character.

After a summer of sandals, sundresses, and socializing, September is the perfect time to reset and get serious.

This week on The Buy, we’re going all the way back to school. Whether you’re starting your year at university, college, high school (or you just like to look smart), fall’s best fashion is collegiate chic with a grungy twist. (Think cardigans paired with combat boots.)

We checked in with our favourite students of all time, from Blair Waldorf to A.C. Slater, to bring you their best back-to-school styles, with all items available in Toronto.

Check out more of The Buy: our picks for the city’s best jewellery, concert clothes, leopard prints and more!