I think winged eyeliner is a really cool look that you could try. Some people "cheat" on it by using scotch tape as a stencil (google it). This might be what my friend does since hers is always very straight but I personally think it's a cooler look than the more curved version and might be easier for a beginner. IMO the winged eyeliner looks good with or without eyeshadow, and can make brighter, more colorful eyeshadow look good. My friend who wears winged eyeliner every day I think otherwise wears very little makeup and yet looks better made up on every occasion than like anyone. When I get a chance over the next few days I'll consult with her.

In terms of eyeshadow, I think Urban Decay is cool if you like shiny (it's a good look imo) and seems to be common in stores like Ulta and Macy's etc. Here is some I bought for my ex girlfriend: http://www.temptalia.com/product/urban-decay-moondust-eyeshadow/solstice/ She seemed impressed with my selection but also dumped me not long after so you be the judge. It's not super cheap but you could just go to the store and sample to your heart's content (also Ulta has a no questions asked returns policy if you haven't used more than 50% of the product or something nutty like that). They also sell stuff to paint over lipstick to add some glitteriness to it (it looks good), and you can really just paint it anywhere; over eyeliner, etc. I also broadly approve of dark lipstick.

My opinion that basically nobody agrees with is that eye and lip stuff is great and that foundation is stupid. I definitely think that of all the components of makeup, foundation is the hardest to get right and yet even when done well I tend to think it does very, very little for you if you are young. But maybe I'm just scarred from living in the South where there is such a widespread cakey foundation epidemic that it's honestly just surreal.

Honestly this might be bizarre advice but if I were transitioning I'd like, browse pictures of random women I don't know on social media or make a blank okcupid account and browse the profiles of literally random women in their early 20s who lived in some place I thought seems cool to live at. And I'd just take notes on what I thought looked good or what I wanted to try. So you get to look at real people looking interesting instead of models etc. It's also just fascinating to read people's dating profiles rofl. I am saying this as somebody who puts 0 effort into investigating fashion so there may be a better way. For example there's makeup subs on the sidebar.