Which brand of leather crossbody bag lasts the longest in the $200–$500 range?

Coach, by a fair margin. Coach uses thicker, higher-quality leather and better stitching, while Michael Kors uses thinner leather and coated canvas that wears faster, and Tory Burch uses softer, less durable leather that scuffs and loses shape quicker. If you want a bag that still looks good in five years, get the Coach.