Not necessarily. Unless otherwise asked, I, like the vast vast majority of people, classify others as men or women or non-binary based on their presentation, because it's the only thing I have access to. If someone wears masculine clothes, and masculine style, and has a masculine name, and I knew nothing else about them, I would obviously say he is a man. If I later find out he was born female, I wouldn't suddenly start thinking he is a woman.
On the other hand, if someone dresses and styles themselves in a typically feminine way but tells me they use masculine pronouns, I will of course by reasons of politeness call them by their preferred pronouns, but privately I would find it hard not to consider her a woman who prefers masculine pronouns.
That's just daft though. Defining women and men in terms of clothing, haircuts and other adornments is awfully regressive. It's like 1950s-style sexist stereotyping all over again.
Well, it's all you've got, ultimately. You can't categorize people just on their word, and you can't categorize them based on any of the biological criteria since you don't know what their chromosomes or hormones or genitalia are when you see them.
And it's not purely about clothes. Even if you look at people adopting more clothing styles traditionally associated with their other gender, say Harry Styles at awards shows, they do not style themselves exactly as the other gender would. Ultimately gender is a social construct, and that involves some shared performance that we each choose to adopt when defining ourselves in relationship to everyone else.
Only if you define man in a way such that any person can claim manhood.
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