While Final Fantasy VII Remake does include an updated take on the original game’s infamous crossdressing scene, there isn’t a way to play as Cloud in a dress throughout the game. Or, at least, not an official way. Thankfully, PC players who want Cloud to keep rockin’ his feminine side have options, like this PC mod…
Source: Kotaku – Cloud Looks So Fantastic In A Dress In These Final Fantasy VII Remake Mods