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.

I recently took a male friend shopping for clothes. Believe me men have just as many fit issues. Also just because a pair jeans says waist X, inseam Y there is still huge variation. Consumer Reports did a report on this long ago.
Or check out this guide from Esquire for men's jeans

http://www.esquire.com/style/h.....ns#slide-1

I'm a hardcore feminist with a boyish build and a pixie haircut, and I really feel that women have the advantage here. Definitely not in the past, but honestly nowadays you can wear whatever you want. Men are so limited! All the guys in my office are mildly uncomfortable all year long in dress pants and shirts with ties. Meanwhile I am quite comfortable in sleeveless dresses and sandals in summer, sweater dresses with boots in winter, and nice pants with tops whenever I feel like it. I don't feel like I HAVE to wear makeup, but when I want to it's great. Men have few options for presenting themselves to the world. I can understand why so many guys get really into their facial hair or lack thereof - because really what else can they do to change their appearance?