For those of you that have known me in real life, most of my wardrobe has always been sort of frumpy. I'd have a couple nice/cute outfits for wearing to shows or special events but then most of the other time it was cheap t-shirts and jeans or denim skirts and mostly plain dresses.
A lot of this had to do with being poor and wearing hand me downs as a child and then thrift shop and discount store clothing as an adult. For a large part of my life, much of it was also related to a religious-based modesty culture that dictated long skirts and dresses, covered shoulders, and high necklines. Add being a plus size into the mix and finding clothes that were nice, affordable, and flattering was pretty hard, so I just bought a lot that was cheap and in my size but didn't really look that good on.
The place where I really screwed up was getting used to it. Even when I ws not following a religion that dictates how I dressed, I had gotten so used to "standards" that I usually still looked the part. Once I was out on my own, even while I was working and making fairly good money, I would go to Wal-Mart or Sears and spend a couple hundred dollars on several pieces of cheaper clothing instead of spending the same amount on one or two nicer things. Where I would have balked at spending $80-90 on one dress, I thought nothing of buying the same $15 top in 6 different colors. This really contributed to my clothes hoarding because I had a ton of clothes that were in good shape so I didn't want to toss them, but most of it was still sort of blah, so I never really felt like I had anything nice to wear.
In the past year or two, since I'va had my son and gone up a size, I've become a much more selective shopper. Part of this is because I am not working outside the home and our family budget has dropped by over half. Having less to stand has made me picky, and that's a good thing. When I do buy clothes now, I am buying only things that I really love and that are flattering and/or make me feel good wearing them. I've found a few local stores and places online that carry clothes I really like and have been slowly upgrading my wardrobe and sorting through my older clothes to give away and sell the pieces that I don't really love. It's made me feel more confident and attractive and my husband has even noticed and offered to buy me more clothes, because he sees I'm finally putting an effort into how I look. The crazy thing is, even with my average piece of clothing costing 2-3x what I spent in the past, the overall amount I've spent on clothing in the past couple years is about a 1/4 of what it was before. Looking and feeling great and saving money in the process - loving it.