The Orly (Osanna) GORE-TEX™ heeled boot from Ara is an absolute stunner. Not only that, it is practical as well. A combination full-grain leather and knit upper is GORE-TEX™ lined, so not only do they look good, but they are waterproof as well. An inside zipper (not pictured) helps get these on and off easily. These are built on Ara's High Soft last, making them extremely comfortable, especially for a boot with a ~2.5" heel. The rubber outsole provides traction on most city surfaces.
Available at Glebe Trotters.