I wear basically the same pants to work every day. I have five pairs - two black, two gray, and one green. They are swooshy. Hooray swooshy pants! I really hate shopping for clothes so when I find things that fit welll, I buy a lot. Most of the clothes I own are from Old Navy and were bought in batches when they went on sale. udandi & the craft of money does the same trick with jeans. I wonder if this makes me boring, that I don't really care that much what I wear most of the time. I do have nice clothes and I like to dress up once in a while, but generally I just want to be comfortable with the minimum amount of fuss. So I have all solid-colored clothes (I almost never wear anything with writing on it) and a lot of black. I generally don't like buying clothes, and I've only had my attention turned to the fact that normal people buy clothes on a regular basis by my dad, who told me to go buy some new damn clothes cause I was wearing stuff with holes in it.
Having all of my clothes look relatively uniform makes it easy for me to put together outfits, and since my clothes aren't particularly dressy or not-dressy, I can wear them both to work and outside of work without looking odd. I wonder though if I am in fact simply boring, that I don't in fact have any particular style, and that is why all my clothes look relatively uniform. You can pretty much guess any day that I go to work what I will be wearing, if you don't specify any colors. Although one of them will probably be black.
Anybody else tried the wardrobe-economizing idea of having all your clothes look the same?