^^here are some of my suggestions. You could pretty much put anything with them but I think that baggier or looser fitting shirts would look best. Tight shirts might make the style look too tight, but you could probably still make it work! Ohhh and on that link, I didn`t look at prices on specific shirts, I just chose them for the look :3
Question #2. What are some good drug store brushes? And which ones should you have?
This depends on how in depth you go with your make-up routine. I usually do more detailed eyes but only use the regular spongey tips and a small flat brush so really not much is needed. I would just suggest getting a small rounded brush for eyeshadow and a thin liner brush for detail/liner. Also a trick is to dip your brush is water first for a more paint-like application process. (I find it easier to get saturated color and define colors that way). Prices really depend on the quality. As you guessed, the higher price the better it will apply the make up but cheap ones work fine for many people!
Question #3. Any good nail colors for fall?
After researching some of the new products online and seeing some of the new nail trends on models or on the street; light pastel blue, shimery grayish purples, dark gray/brown, and peachy colors are painting the hottest nails nowadays. (: