My strategy is simply not to buy the stuff that I find uncomfortable (well, if I can help it -- obviously, mistakes creep in) and/ or not to wear the uncomfortable stuff when I am going to have a long day on my feet/ in the public eye.
I find pants and skirts/ dresses equally comfortable OR uncomfortable -- depending on the variables. Fabrication, length, cut -- and weather -- are all important factors. So I have to keep in mind what works for me in a specific situation.
It's true -- that means I have to do some mental juggling sometimes. But overall, I'm really glad I have these options.