I won't say that I don't care how I look, because I always try to look neat and tidy, though I don't always manage it. I'll admit to the wash and wear hairstyle -- I've always hated futzing with curling irons, etc., though I will from time to time for special occasions. Sometimes, I cut it shorter, sometimes let it grow longer with just a trim. I usually wear makeup, until I forget and go for weeks without any at all. I hate shaving and will go a long while without bothering if I can get away with it.
I do pay more attention to my clothes now than I ever did in the past, partially because I lost a lot of weight and had to buy new clothes and partially because I'm starting a new professional career and want to look the part. I won't let myself buy T-shirts anymore because if I have them, it's all I want to wear, since they're so comfortable. My daughter tells me that my everyday clothes are nicer than most people's semi-casuals. I even own a couple of dresses and skirts, now, and wear them from time to time by choice. So, I guess my wardrobe is growing up a bit.
I'm actually very careful about the fit of clothes, but what I like may not be what others would prefer. I'm still getting used to the form-fitting pants and tops these days, but I make sure that shoulder seams are at my shoulder where they belong and that button plackets don't pull in the middle too much. I'm not so great about hemming pants legs, though.