>>5
Stick with skirts, it's hot. However drop the band-tees, that's not so hot. You could go with jeans too, and I personally recommend either buttoned collar shirts or sweaters with high collars. I suggest natural colours for clothes, I like the natural look, it's easygoing.

As for makeup, fuck it. Know what, tend for your skin instead, and I don't mean smear your face with tons of creams and all that crap. Don't finger your face, wash your hands with soap regularly(but not your face, wash it with water only after you've washed your hands). When you take showers you can wash your face with shower gel. Have a healthy diet. Exactly what that is varies depending on needs, but you can do some research. Drink a lot of water though, it washes through your system.

Exercise daily. Start with walks, 30 min a day if you can fit it in. Bicycle if you can, do it much. Go for a jog every now and then but try for excercises that go easy on your legs and knees especially. Go swimming often and take steam-baths, it's also good for your skin. Aim for losing some weight, it will be good for your self-esteem as well as your health.

Overall I think you should go for a natural look, so don't worry about makeup and dressing your hair. Grow it long, at least shoulder-length, and you can have it put up in a pony-tail or some shit, that's always cute.

Your appearance is a good place to start, and losing weight should be your main focus atm. But don't resort to things such as starving yourself, taking pills or anything, do it the right way. It will be rewarding in so many ways once you start to see results.