I love dressing up in my riding gear, I like the look of jodhpurs but I do like my stiletto boots more than riding boots. I've broken quite a few riding crops in my time, they never seem to last that long around me!
I have a large riding crop which is very good at making bottoms red as it covers such a larger area. I have lots of other riding crops and various dressage whips, which all deliver a nice sting.
See some of the bottoms I have cropped on my Bottombook.