I really don't do overly feminine clothing and feel really awkward in dresses and heels. It feels crossdressing, even though it isn't.
I have lots of men's shirts, unfortunately it's really hard to find fitting pants since I have really huge ass wide hips.
To go all the way, as in tape away tits and everything, would be lot of work though. Still, I think I would if someone wanted it for sexual or other reason, and I might even enjoy it.