Maybe I'm on the other end of this, but I think the ultra "casual" (read...lazy and sloppy) look is just not flattering. I live in a white trash, redneck sort of area where people go out in pajama bottoms and flip flops, and it just isn't a good look! Like it or not, you are judged by how you present yourself to the world. Employers who don't like your look won't hire you. You are free to dress as you please, but don't expect to conquer the world (or even get that job....or guy....you have your eye on) because we ARE judged by how we look. Now don't get me wrong, you don't need to follow all the latest trends and go all out with wardrobe, makeup and hair. However, making yourself presentable can go a long way. If you go for a classic look, you can keep the same clothes for years and thus you aren't really spending a lot of money or time to keep up with trends. The same goes with makeup. You can do simple things and develop a routine that only takes a few minutes out of your morning. You get a haircut that is simple yet stylish. All of these things can make you a lot more presentable (while still remaining comfortable!), with minimal extra effort.