>>18486320 (OP)Always buy men's pants for the cut / fit. It will signal that you're experimenting for stylistic purposes, not some sort of ideology reason. It's kinda dumb, but 30 years ago you could just play around but now with the woke stuff you have the make a point of "I'm a fashion person, not an identity person".
The key is to focus on what pieces really call to you; I'd say even knee-length skirts can be worn by a man, but you need to stick with men's pants when going with pants. The problem is woman's pants are going to cling to you in socially-awkward ways that draw the wrong kind of attention.
And when I say "wrong kind of attention", I'm not talking about gay or straight. I'm talking about people worrying if you'll want to focus on having a politically aggressive argument.
The truth is most people in 2025 don't care which way you swing, or what you identify as, but they are tired of politics being injected into everything. They're a bit hyper-worried, so it's important to somehow convey that your deal is soley about fashion and not some kind of a reg flag.