Truthfully, I only go horseback riding once every year or two, on family trips to North Carolina. I don't know much about what the hallmarks are, exactly, of a "real" equestrian boot. But I've come to develop a pretty good sense of what so many of us love about equestrian-inspired styles that get it right, and I think the word is "grace." They're sporty but not sexless; strong but not severe; simple but not boring; luxurious but not showy. You put them on and start moving around a bit more fluidly. At least that's how this sleek, Spanish-made boot feels to me.
Calf slimness: ***/5
Find it at:
Alas, ebay looks like the sole source as of fall 2016
Note: The Equine is a real riding look. But if you're after a more fitted ankle and "legging boot" style shaft, you'd probably be happier with the Mezzamezza (right), a knee-high version of Weitzman's cult-classic 5050 but with an inch more heel to flatter the leg.