These Disney dudes look like a lady. Could use more ladies disguised as dudes, though.
"The Three Caballeros" - 1944
Oh Donald, the come hither off the shoulder look is overshadowed by your lack of pants.
"The Adventures of Ichabod and Mr. Toad" - 1949
Honestly. Mr. Toad, who plans a prison break in heels? A man, that's who.
"The Jungle Book" - 1967
Did Baloo know King Louie's taste in women(?) ahead of time or did he just get lucky?
"Robin Hood" - 1973
More like Robin Hood: King of Fabulously Bold Color-Blocking.