Gutmutter, we can be twins with our *ahem* "style". I've got it going on too, even the men's shoes!
I do wear makeup, most days...my job is so nasty, it helps me feel a little bit better!
Otherwise, I agree, comfort is THE big thing for me, so I usually end up looking like an old hippie or beach bum. That can fade over into "outdoorsy" if I'm on vacation somewhere that you need to layer up due changeable weather.
I can do dressed up, but I'd usually just rather not. Unless it's Halloween or something and I'm dressing up in an actual costume! Or if I'm feeling kind of silly that day and wear some of my pants with wild prints, or overalls or something in bright colors.
For work, I wear loose fitting jeans, and the t-shirts too worn out even for yard work, and the whole getup is stained in every color you can think of...no style there, unless 'bag lady' is a style. I've had people offer me spare change as I go in to work .