Generally women dressing as men aren't perceived as threatening, or challenging.
It was different in olden times, than it was coined "unladylike", akin to a fallen woman.
Basically oldies feel threatened as their own ideas of traditional masculinity are threatened. Roles are set. How dare anyone demean a man.
Heard of Culture Club? Because people thought he was a she, because of the whole image he created, George put "Boy" in front of his name so there would be no mistaking it.
On the other hand Eurythmics' A Lennox dressed as a man.
However sometimes men can't pull off the look. It's obvious there is something amiss. There is an art to looking feminine. It takes work. Knowing what suits their body shape, to enhance it. The overall package, makeup, accessories, the slinky walk.
Some women who are tall and are uncomfortable with their height always looking down, as a consequence too can look uncoordinated.
It's looking smart, and being comfortable in their presentation. Acting natural. Feeling relaxed.
Would you say both are men or women? Both are the same sex.