Ankle boots are the workhorse of a good wardrobe and we mean that as a compliment. They carry an outfit through the awkward in-between seasons, work with dresses in a way that taller boots rarely do, and manage to look considered without trying too hard. The problem is that not all ankle boots deliver equally. Some look incredible in photos and destroy your feet by noon. Others are comfortable enough but so unremarkable that they disappear rather than contribute. We have no patience for either. What we’ve pulled together here are the ankle boots that actually earn their place, the ones with enough personality to improve an outfit and enough construction to last more than a season. Block heels, flat Chelsea styles, pointed toe options with a modest heel. We’ve been ruthless about quality and equally ruthless about style because the two should not be in competition. The right ankle boot does not ask you to choose.