I can see a lot of potential with this thread as a guide of sorts for girls who need makeup and hair advice, but lets start with my issue.

I have no knowledge of how to wear makeup. I remember as a little girl I put on so much blush my mom had to wipe it all off before I went outside. Then in middle school, the only makeup I wore was gold eyeshadow that I wore every day until I was bullied so much for it that I stopped wearing any makeup. This was a blessing, as I became so used to not wearing makeup that I feel "naturally" beautiful. I remember that there was a Full House episode when one of the girls was interested in makeup and was told that the best way to wear makeup is to look like you're not wearing any makeup. In that case, I decided to stick to being naturally beautiful...until now.

Within a few weeks I am planning a major makeover. My job allows me to cut and color my hair however I'd like, wear any style makeup, and have any kind of colored nails. Once I have the makeover I am having my photographer friend stage a photoshoot and prepare myself to walk into work a bolder, edgier, more confident me.

This is the style of haircut I am getting:



And I am getting this color with streaks of pastels blue and purple:



And I will be picking out a pair of square "hipster" glasses (I have an eye exam coming up and get to pick new lenses), likely black or maybe brown calico-colored glasses.

Now onto the makeup portion.

I really don't know anything about makeup, what I need, or how to apply it. I know the basics of what the lid, brow, and crease eyeshadow is and how its used. I did a bit of quick research on how to where makeup while having glasses, but I'm still not sure what cosmetics I'll need (since in the article it's $20+ each). I definitely do not want to spend more than $20 for everything, so I'll also need help on which brand to get.

This is the most current photo of me:


This is a much older photo of me with makeup on, a closer picture so you can see my eyes and features better.



I don't think I need to do anything with my eyebrows except to tweeze them and shape them a little better (I know the basics on how to do that).

I'm debating which color lipstick or lip gloss to use. Since my work allows any kind of makeup, I want to be bold and edgy, but still professional. I usually work in the daytime.

This is the style I'd like for my eyeshadow in gold, but I don't know what to buy or how to apply it to get that look:



In one of the articles it said that for eyeliner it must be one or two shades lighter than the color of my frames. What color should I get if I get black or calico brown?

They also said to use foundation/concealer, but that's way over my head. I have no idea what I need. And I'd probably have to get blush or bronzer, which is also something I am clueless about.

Any other suggestions or advice or things I need to complete my new look? Thank you so much!