it's not that caitlyn's s1 outfit wasn't dress-like. it's that the moment she had ultimate freedom to choose, no expectations on her whatsoever, no one above her, no one to tell her what to do, no one who would judge her for it, she went straight to the turtleneck and the pants and then continued to stick with them after everything was over.
that's what we mean by her making the choice and that's why whenever people fall back on that s1 enforcer outfit to argue that she would be ultra feminine that it feels strange.
I don't think she'll never wear a dress. I do think she is capable of femininity, of course. and I think she'd look really hot in a dress.
but claiming from her initial enforcer outfit that that's the pattern of what her heart desires? c'mon now, the whole thing with s1 caitlyn was that she didn't have what she truly desired, which was to be seen and taken seriously for her skills and not just what people saw or recognized at first glance.