There's a strong difference between something like the Flame Elite's outfit, which has a skirt but looks more like a slightly revealing robe when worn, and isn't NECESSARILY feminine on its own (also note it's caster gear, casters get a LOT of leeway when it comes to things with skirts), and the wedding dress, Spring Dress, Bunny Outfit, and now this outfit. See, the former outfits are "gender neutral with a feminine flair," while the other outfits are strongly feminine. I know it doesn't come across this way to some people but that's pretty much it right there.
Here's the thing: Those weird things they're known for? Yeah they're weird to THEM too. You know how we watch shows like Honey Boo Boo or Jersey Shore while still mocking them and anyone who adheres to that lifestyle? It's the same thing.
The thing is Japanese culture can be extremely passive aggressive about this sort of thing.
Is it the strictest place on Earth? No, but there's an interesting reason why.
See, you're supposed to keep your predilections private, and ANYTHING that becomes public reflects on your family and co-workers. There's an entire movie based on this sort of thing that's readily available (and even got made into a Richard Gere film that lost some of that meaning) called "Shall We Dance?" Yes that's the Japanese title too. In it, a regular salaryman takes up ballroom dancing. Yes, simple ballroom dancing. However, because of the risk of his wife and job finding out and getting him ostracized, he has to keep a secret.
Thus, here's how it would play out if SE started making outfits that bridged onto ACTUAL crossdressing, rather than the grey area of the Flame Elite's outfit or Scylla's robes:
"Yes, I work at Square-Enix. I helped make Final Fantasy XIV."
"Oh...isn't that the game that was on TV yesterday where your character is the giant green man in the bellydancer outfit?"
"Umm..."
"That's kind of gross."
This is also a major reason why many actors, artists, and creators use pseudonyms even when making something innocuous. Any stigmas that get attached to the work get attached to their personal lives. So, the intention here is that they must keep their personal and professional lives separate.
Something tells me something like this happened after Final Fantasy VII, because that's the last time I remember there being male-to-female crossdressing in the main series final fantasy games.