I think it's always very important to be comfortable and just kind of expressive; if you take fashion too seriously, then you lose the fun of it. I think you should always take the risk.
I try not to wear foundation unless I have a giant pimple, which sometimes I do. For the red carpet, I may add a brighter colored lip and darker eyes. But my standard is blush and mascara.
I'm only at the beginning of my career, but I feel successful in that I haven't sold out in any way, shape or form. I feel good about the choices I've made, and I don't feel like I've let go of any of my values.
I am a huge, huge fan of the plain white tee. A good-fitting, vintage plain white t-shirt, like the 'boyfriend shirt', is the sexiest thing a girl can wear. It goes with anything, fancy or casual.