I trail ride in a dressage saddle. I love riding tights-never ride in anything else. The very few times I've ridden in jeans when I happened to swing by the barn unexpectedly coming from somewhere else, I found that very uncomfortable.
I am short (5'3ish) with short legs, small feet, and unfortunate man calves. Kerrits brand fits me the best of the riding tights, though even they are a tad too long so I have to be careful the tights don't bunch around my ankles. Online tack shops like Smartpak or Dover often have great end-of-season sales on them as long as you don't mind weird colors like plum
Given said man calves and tiny feet, boots are problematic. I can't find any tall boots that fit me and there's no reason to custom order since I don't show. The one exception are a particular style Ariat of insulated winter riding boots, which just barely stretch enough to zip up. I wear them from Dec through March. In the summer, I just have basic Ariat paddock boots and use Dublin Easy Care half chaps (again, the only option I have found that is short enough to not come up over my knee but wide enough to zip).
It took me awhile to find what was most comfortable, but once I did, it made shopping super easy because now I just replace what I have when it wears out with the same thing!
: if you're on Facebook, check out "Safe Riders Gear," they're a company in Vermont that makes most of their stuff in the US and has hi vis breeches, vests, and other brightly colored/reflective stuff for horses and riders.