Only worn a few times! Even if you already have a million black ankle boots (or two million, rather), Western-inspired stitching punches this pair up a little. The shape is slim through the ankle for a sophisticated, not-so-costumey feel... more Chelsea cowgirl than rodeo queen. Ann wears hers a couple times a week, if that gives you any sense of the utility. They're just easy. These are bench-made in Spain — talk about a cultural mashup — with Goodyear construction, a stacked heel, and a pointed, slightly squared-off toe.