Most of the time, I wear whatever is clean, and prefer baggy clothes because it's comfortable. My favorite is sweats and t-s. I don't care if I buy some cool pants that say "beautiful" on the butt, as long as they are comfy. In fact, sometimes I've gone grocery shopping in pajama pants just because my sweats were dirty and I wanted to be comfy. I do get attention that way, even though I don't really want it.
In work place scenarios, I usually wear brown and gray and black. I try not to wear too much red because it's a power thing to wear red according to some interview guide thing. Brown and gray are best for blending in. Navy too, but I don't like that color on me. I like black because it's thinning, and you can easily find black pants with a spandex type top which is so much more comfortable to me when the pants can move with me without falling off.
Now when I go to the club, I wear tight black pants that come out a bit at the feet (loose fitting almost bell bottom but not quite that bad). I either wear combat boots (with a good shine) or these boots I have with a pointy toe and high heel. THen I always wear a bright colored shirt that is very revealing or tight. As long as I think I look like a supermodel, I'm cool with it. I love the attention then because I don't go out unless I'm in the mood for some. Lately though I don't feel as pretty. I just don't feel young anymore now that I have kids. It's like my body went from Booyah to Blah. I don't get the attention anymore that I once got.
Hats is something I am always afraid to do. Also the doo rag type thing as well. I'm just warming up to it. I can only do that when I feel brave, or if all my friends are wearing the same type of hat. I do try to think of Denise's character from the Cosby show...she looked good in every strange style she wore. So I figure, it may look a little stupid, but I'm so good looking that I make this look good. Doesn't always work, but that self talk gets me to be a little more brave with style.