I'm definitely not against cross dressing. However, Eorzea is a different world with a different outlook on characterization. There seems to be a line drawn when it comes to identifying as a male or female, and as a Japanese game, their culture is pretty evident in the game. Hildebrand clothed in a dress was for comic relief, nothing more. Even the weddings can't truly be considered LGBT, as the Dev team has very specifically steered away from "Marriage" to a generic "Bonding." Being a video game, FFXIV has been very forward thinking, and compromised due to the collective fan base's requests. There's still a long way to go in the real world when it comes to gender equality, a MMORPG isn't going to be the groundbreaking civil rights leader.

That being said, that dress is fabulous. But I doubt wielding an axe in a dungeon wearing that garb would be easy, tripping over the hem every time you throw up a berserk.