I love this, Yael. I am approaching 40 (38 since July), and I, too, have only recently begun stepping more into unapologetic self-expression with respect to fashion and makeup. Relatedly, earlier this year, I also began posting photos of myself topless and/or completely naked on social media (Instagram, but also a few on Facebook). There are a lot of personal and political reasons why I have chosen to begun doing this — so many that I started writing an essay about it recently (which, alas, my current workload at my day job leaves me too busy to finish for another month or two) — but many of them come down to how pissed I am that the patriarchy doesn't allow women to truly OWN our bodies. It also punishes those who are considered conventionally attractive, as well as those women who dare to enjoy their appearance and appeal.
As if the physical side of self-love were a terrible sin. And as if pretty (or sexy) packaging automatically cancels out any spiritual or intellectual strengths the woman contains. The idea being: women's value goes absolutely NO further than our sex appeal, because sex appeal is what cancels the other values out and renders us personally inconsequential. The flip side of that demeaning attitude is the fact that the patriarchy automatically deems women who are recognized for their non-physical qualities (e.g., intelligence, kindness, or spiritual richness) less desirable — and, therefore, ostensibly less worthy of respect — as partners. Such bullshit.
Keep wearing what you want and pushing the envelope. Thank you for doing you. :)