A big, baggy teal sweater. It's old and starting to fall apart. And it has paint on it. Even I will admit it's ugly as hell... XD But it's so warm and comfortable, I can't get rid of it. Plus it makes a good painting smock. But I've never worn it past the end of my driveway.
And then there's my favorite pair of jeans. They're about six years old and faded, a tad too big, and they have holes in them and they're also covered in paint (but it's harder to see on them). I wear them when I go hiking or fishing, or I'll wear them around the house. And sometimes I'll wear them when I go to the grocery store or something. They're comfortable. =3
Both of these items have become my "painting clothes", which is the only reason nobody has thrown them out yet, I think. XD This is also why they're covered in paint to begin with. The pants, unfortunately, ended up this way on accident. ;_;
I also have my dad's old camo jacket, from when he was in the Marine Corps. It's not the most fashionable thing ever, but I love it, and I use it as a jacket from time to time. Nobody complains about that one, though. =)