I work in IT, I make much more money than I should/need and I work from home in a pair of basketball shorts and a T-shirt while barefoot. I would just apply for everything, eventually you’re gonna hit someone who isn’t hung up on image, and the rest will make your interview skills just that much better.
My work history is ok; I have solid interview and writing skills, which is more important to most places I think. Mostly because I apply for a lot of things I’m not really qualified for or that pay too little just for the interviews.