While I love all of my many pairs of Ariats, I've found I'm way more comfortable long distance riding in my Keen hiking shoes. I have both the summer and the winter boots that go over the ankle. I can easily jog lightly and they are super on steep downhill jogs. My feet rarely go numb with them. I love the wide toe box. I always ride in EZ stirrups with safety cages. My "other" favorite shoe to ride in is my trail running shoe-Montrail Hardrock trail runners. They just don't have the nice ankle support of the Keens. Every one is different. You'll likely have to spend a lot of money to figure out what works for you. Cindy