I saw a pair of boots by Tom Ford last year that took a hold of my imagination. I've never been as taken with a pair of riding boots before I saw those. What made those riding boots so unique was their combination of the classic shape of a riding boot with some of the grittiness of a motorcycle boot. Unfortunately aside from the chance meeting at Bergdorf Goodman's, I've never been able to see those boots again. That hasn't kept me from looking for close substitutes. I feel like the following examples would fit right in on the trail.
Rogan x Frye