On one hand, the driver should have known the context of "lolita" stuff being super creepy.
On the other hand, if he was wearing any other fun costume, and not cross dressing, this would not have been a problem at all. There's nothing inherently wrong with drag. There are well respected Toronto comedians that wear drag for characters and they are great.
The rise from starter job to top government official usually includes things like gaining experience, having some success, being a noteworthy professional in some way....
Not... Nothing?