I can't wait to see your new look! It sounds fabulous! As for makeup, since you're so young and have such good skin, that I don't think you need heavy foundation or concealer. If I were you, I would go with a lightweight foundation or tinted moisturizer. Your photos don't show dark circles under your eyes, so you don't need much concealer there. Since your hairstyle and glasses will be bold, I would go with simple eye makeup. I like the photo you posted of what you like. Take it to a makeup counter at a department store or makeup store and ask them how to do it. I think you would really look good with the cat-eye style eyeliner. That does take practice to do well. There are plenty of video tutorials on that. Lastly, I would opt for bold lips to balance out the bold hair and glasses. It doesn't matter what color. Just whatever you feel like and looks good on you.

Drug store makeup is fine to use. It can loop just as good as the expensive stuff. It's all in the application, and practice makes perfect. I like to shop in discount stores like Big Lots, TJ Maxx, etc. for makeup. More bang for my buck. If I don't like something I bought, then I haven't wasted much money on it.

I also like to buy face wipes from Big Lots. A whole pack of 30 costs only a few dollars. It doesn't get all of my makeup off, but it does get most of it. That way I use less of the somewhat expensive cleanser that I have. (I'm 47 and use an anti-aging formulation.) As Christina said, you really need to wash the makeup off completely every night before bed, or you could wake up with a very pimply face the next morning. A good cleanser to use is Cetaphil or a store brand equivalent. Very good for sensitive skin and relatively inexpensive. If you have large pores, you may want to use one of those battery-operated spinning brushes to help remove the foundation. It's gentle enough to use every day and doesn't have to cost much. You can buy expensive systems for $100+ or you can buy the cheapest thing on the market. I think both will give you the same result. Wal-Mart online has one for $27. From your photos, it doesn't look like you have large pores, so I don't think you need to worry about it.

Have fun and post pictures!