What if a 'women' has a different internal gender (no offense if I don't know the lingo, very supportive of LGTBQ), and would be more comfortable dressed in a pant suit or even a Tuxedo? Or some other stylish more in-between thing that still looks nice and could be considered 'dressed to the 9s'.

I can see where this could be offensive as some women don't like short dresses, not everyone is comfortable showing off their legs either for one reason or another...

It should've just said Dress like you're going to the Oscar's or something -without giving direction as to what that means.