I mean, it's obviously good to come to an understanding of why it wouldn't work for oneself in particular. But if you see something in a wide range of people? I'm wondering if there's a way I could be convinced to at least like something on the rest of the population, even if I'm positive it will never work for me.

To be honest, I've yet to see an example of a shirt dress here or elsewhere on the Internet that really warmed my heart. I guess I care enough now that I'd like to know why trend X rings a bell and trend Y doesn't. With the shirt dress, it just looks like a too-big shirt. Ymmv.