There are only a few cross-dressing movies that get away with the tired concept and those that usually do get away with it make some kind of an effort to rationalise the necessity for a dude to put on the dress. He’s My Girl skips all this and just goes for the lowest common denominator bloke in the high heels approach.
As sad as it sounds, the whole cross dressing act is also the strongest suit of the movie. T.K. Carter actually has the voice and the looks to pull off his sassy transvestite act, and it’s the rest of the movie and especially its cast that falls far behind. Very far.
It’s hard to justify why a movie like He’s My Girl should exist as it doesn’t really bring anything new or original to the table, nor does it manage to make one laugh. This is one of those movies that the time forgot, for a good reason.