While the typical "back to school" look means coordinate sets and loafers or pumps, you can breathe new life into a skirt suit when you finish it with sneakers. I wore my H&M corduroy blazer ($60) with the matching bottom ($20, originally $50) and played up the blue tones with Ash Addict trainers ($275) and a POPSUGAR at Kohl's cobalt crop top ($20, originally $30). I felt like a '90s mom on the way to the office with my grandma's vintage Fendi purse, which I actually feel like I should refer to as a pocketbook, just for kicks.