@RFAAOATB - as far as wearing men's pants goes.. I've thought about trying to find some of those super tight hipster jeans to see if they fit me just so I can have pockets. If men's skinny jeans can have pockets why can't mine??
As far as general clothes shopping goes, last year before I found MMM I spent about 1000$ on clothes. I will accept all face punches, and here come my flimsy excuses. I had recently entered the work force and also built up a bit of cash (even in my non Mustachian phase I had an emergency fund), so I felt I could do it. I also hadn't shopped in years, and all my clothes were ones that my mom had forced me to buy in highschool. What everyone says about finding a fit that is flattering for you is true, and I've always hated shopping because finding a good fit was always super hard for me because of how petite I am. To give you an idea, I once was looking for a pair of khaki pants and upon finding a cute pair I showed my Ma. She took one look and burst out laughing because they were supposed to be capris (not pants).
Anyway trying to keep it short, but last year I stumbled upon this place called White House Black Market. Very classic looks and one of the only adult professional clothing type stores I've found that has xxs and 00 pants. Plus their employees help you put together outfits and suggest things that would look good with what you've picked out. I know its all so that you will buy more, but honestly I always feel so lost when I'm clothes shopping that I love just having someone do it for me. Oh, and also their clothes seemed like much better quality than some of the other stores I'd seen. Maybe I was going to the wrong stores but in the other stores I had been to the fabrics seemed SO thin! I was thinking it wouldn't even last me a year.