I also have a hard time finding clothes that fit me right, so I end up with stuff that I just love but it looks weird on me. I'm 5'7", but I have a long torso, so I have to buy "short" length pants. Sometimes I will find pants that fit me right, in length, but then they gape out around the waist. Buying pants is an all-day thing. Last year, I found a good style of jeans that fit nice, at H&M, so I sent my friend who works there some money and she got me several pairs, so I don't have to worry about jeans. Sure, they all look the same. But they also fit, which is the most important thing for me.
Also, with shirts, I have to get something that's extra long. It is much easier now, since it's the style to wear extra-long shirts, but it used to be all the "normal" stuff would stop an inch above where my waistband ended. Which isn't really ok for a girl in her 30's, and is *completely* inappropriate for work. Still a problem, if I find a shirt that fits around my chest, it's really baggy around my waist and looks like a sack.
I used to keep all my clothes, even if I hadn't worn them in a long time or if I'd gained weight and they didn't fit anymore. I had that nagging "but maybe some day I'll need this...." in my head. But then I realized I had a closet stuffed full of stuff, and I could only wear a few outfits. That's when I purged my closet of unneeded things, and gave them to the Goodwill, so I hope someone got to use them. I allow myself a tiny section of Nostalgia, things that I love so much, and have memories for me. Then I went to San Francisco and had my friend help me pick out a nice new wardrobe.
I do still have lots of clothes, I have to keep my off-season stuff in the closet in the guest bedroom and switch them out. But I can, and do, wear most things now, so that's good. I did buy 3 or 4 sweaters this winter, and a few long sleeve shirts, but I did really good on not buying a bunch of stuff I don't need.