I see a lot of casual trans Zoro art and headcanons which is cool and vibes but I feel like we're missing the opportunity to think about how cool specifically ftm Zoro would be as an actual major plot point specifically the way One Piece handles stuff. So here's my headcanon for how it would fit into the story:
Zoro who always just knew he was a boy. Zoro who introduced himself to Kuina and the dojo as a boy because puberty hadn't hit so nobody could tell the difference. Kuina who told him he'd end up better than her no matter what because he was male. Zoro who snapped back that he was born the same as her and he's going to be the best anyway, removing her excuse and inspiring her to keep trying.
Kuina still dies. Zoro still inherits her sword. Her father doesn't know Zoro's secret.
As his time at the dojo goes on, he starts binding. It gets harder to hide, and it's not healthy for exercising. His voice isn't lowering the way a teenage boy's is supposed to. But he keeps up, because he will be the greatest swordsman, and he will do it even with a body people don't believe is capable of it.
When he gets older he learns that there are medicines and surgeries some people get to change themselves. He wants that, if he's honest. It would make things so much easier. But he decides to wait. As part of his promise to Kuina, carrying her spirit with him, he vows to become the greatest swordsman in the body of a woman.
At some point, though, Koushirou knows something is up, and figures out that Zoro is (in his eyes) a "girl." He feels betrayed, his pride injured, having poured so much into training his prized student only to find out he inevitably will be weak as an adult. He had even considered having Zoro inherit leadership of the dojo, and now those plans are wasted. He confronts Zoro angrily, seeing no irony in the fact that both he and Kuina were always the best in the dojo, because his misogyny runs too deep to change his view now. He refuses to keep training Zoro unless he "admits he's a girl and trains accordingly."
Zoro is furious and devastated, but he won't give up his goal or pretend to be someone he's not, even if it costs him acceptance and mentorship. He rejects Koushirou's ultimatum, and sets out to sea, starting his bounty hunter career just like in canon.
When Luffy meets him, he doesn't question who he is at all. Honestly he doesn't even pick up on anything different. Nami notices, but keeps it to herself. Usopp just kind of assumes Zoro is younger than he is based on the voice.
Sanji, however, thinks something is weird about Zoro from the start, and it drives him crazy. He acts like a man in every annoying brutish way, he certainly smells like one, but his body and voice seem different? And why does he exercise SO MUCH? Sanji has not unpacked any of his own gender issues at all and is incredibly rude about it, pestering Zoro until he finally explains it to him like he's five. Sanji is shocked, and asks without a hint of self-awareness, "Why would you WANT to be a man when you could be a beautiful woman??"
Zoro files that fascinating thought away for later knowing there's no way they can unpack it right now, and just asserts, "I AM a man. It's none of your business why. It's just how I've always been. And if you have a problem, you can fight me about it."
Sanji has some self-reflection to do, but eventually sort of settles himself into the reality that Zoro is a man in every way that matters. Everyone else accepts him as such, and while he might not understand, the way Zoro interacts with the world certainly doesn't feel womanly. So he continues to swoon over Nami and Robin, and fights with Zoro just like in canon. They're evenly matched, and he begins to enjoy their rivalry.
The rest of canon doesn't need much alteration unless we're exploring trans/genderqueer Sanji, but that's an entire post in itself. Basically part of Zoro's dream is that one day he'll have the body he wants, as well as the title. It might seem controversial to have a trans character intentionally wait on medically transitioning just to prove something, but I view Zoro as someone for whom medically transitioning is secondary, almost cosmetic. He's confident in himself as a man regardless. And some kind of hard-line dramatic promise like that is perfectly on brand for him. I also think it honors Kuina's legacy by really proving that it could've been either of them, and the difference between man and woman isn't important when it comes to great swordsmanship.
It would also add another somewhat funny layer to the interactions with Tashigi, who fully assumes Zoro is being sexist and he never gets the chance to explain that 1. that wouldn't make logical sense and 2. SHE LOOKS LIKE HIS DEAD BEST FRIEND OK??
Anyway that's the gist of it. Feel free to add thoughts.
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