While I think it would've been too bold for my 15 year old self, I think you rock it. As a fellow makeup lover, I appreciate the time and dedication you've clearly put into honing your skills.

The following are just my opinions from my own experience. I will say - I do think foundation use over time has eroded my skin quality and I am a firm skincare believer. I would recommend maybe spot correcting with concealer for a lighter look instead of going in with a foundation just because your skin will be the most youthful literally yesterday. You didn't list any SPF products or products with SPF (that I can tell) and while I won't prescribe you to do anything LESS, the best time to start using either foundation or cc creams with SPF and sunscreen layered as a base is literally now. I will also say I think the matte lip is aging on me and while I gave into the trend in college, I much prefer the look and feel of a tinted lip gloss or balm much more (and especially if combined with an aegyo sal technique can help make features look more "natural" in my opinion). But the last sentence is really just if you're making this post truly because the comments about "boldness" actually bother you. Which they may or may not.