To me, loafers always felt preppy (or reminded me of Thriller-era Michael Jackson). But for our most recent hair tutorials, my friend Caroline wore patent black loafers with everything from jeans to dresses, and she looked effortlessly cool and tomboyish. This cute pair also comes in oxblood. I'd love to wear them every day this fall, wouldn't you?
P.S. Parisian wedges.
(Photos of Caroline by Jamie Beck for Cup of Jo. Jeans are vintage Levis; baseball tee from J.Crew; green men's jacket from Nicholas K, and striped dress from Madewell)