I hate clothes shopping. HATE it.
My problems began when I was full-grown at age 12. What was fashionable for kids my age didn't fit me. They didn't have much of a "juniors" section back then, so I had to shop in the adult women's section. So I had to dress "old" pretty much my whole life, or have my mom make my clothes for me. To say I was unfashionable was an understatement.
Now with the sizing and not really being able to fit exactly into any style, it is near impossible to find clothes that look right. When I try on clothes at the store and think "I look better naked than with this outfit on", that's really a problem. Clothes are meant to enhance, right?
I do know how to sew, though it is not my favorite thing to do. If I could keep all my sewing stuff set up all the time, it would be less of a problem because it is such an ORDEAL to get it out and have it take over the kitchen only to put it all back again... But, I have really come to the point that if I want clothes that fit right and look good on me, I'm going to have to make them myself (this time, as an adult, picking out my own fabric and patterns...)
I go clothes shopping as little as possible, which is every couple of years. Shoe shopping is more often, but not more than twice a year. Basically, I only go when I am desperate and the clothes I have are starting to literally fall apart.