Thigh-high black boots are a fall outfit investment. You’re guaranteed to wear them year after year after year. Plus, this season there are plenty of exciting options that you definitely don’t already own. You can opt for heels or flats. Patent thigh-highs will look great with bike shorts. Suede ones will add even more texture to a teddy coat look. Slouchy boots have also risen from the graveyard of middle-school trends and look especially nice when paired with your favorite pair of denim. $495, Labucq Babs Boot. Get it now!