AJ, you look great and I love the creativity in your outfits!
I'm 38 and my monkey shirt went on the thrift store pile last year. I was dressing a little too young at times, still shopping in juniors and that sort of thing. I have a youngish face and body also, so I wanted to find ways to elevate my style and look my age. I also wanted my career to move along and be taken more seriously. My mom would say "you still look like a teenager" and later insist it was a compliment, but for some reason it didn't feel like a compliment.
Part of the reason I was dressing that way was that sometimes I didn't feel like a grown-up inside, despite being married, having a career and a mortgage. I had cute down pretty well, but I didn't really feel comfortable looking like a woman. I equated grown up with matronly.
But it's not like I squashed my basic instincts on how to dress. I just reminded myself to try to look for nice fabrics and grown-up cuts. I found role models like Audrey Hepburn who looked young, but still super sophisticated (not that I'm whipping out cocktail dresses, but you know what I mean). And one day the monkey t-shirt was in the thrift store pile and I didn't care.
We're all on a style journey and only you know the answers! I just thought I'd share my own process in the last few years. I absolutely love your creativity and hope you won't squash your individual style! It's so inspiring!