Sometimes when I log in, my characters on the character select screen are wearing old transmog looks. Why does this happen? Does the game not always save it correctly the next day? It’s one of those bugs that I always notice but forget about once I log into the game. Not a big deal, just find it odd.
Does this happen to anyone else? I assume the new Warband screen will fix it, or at least I hope.
A friend keeps saying that whenever he logs on, his character is wearing his cooking gear.
Well, your toons have lives outside of the game just be glad you don’t catch them when they came out of the shower.
It happens to me all the time.
Or we’ll have four characters in wrong transmog. 
That’s always been an issue. After I change outfits often times I have to log the character in a few times before it appears on the Character Select Screen.
My guess, there are two places where your outfit is kept, one that supports the character select screen and one that supports the in game information.
If that is the case, then when you transmog it obviously updates your outfit on the in game server but it takes time to get around to sending it back to the character select server.
Its probably in the cache and my experience has been it takes a few days to write an update . I do not know server mechanics , but I am sure there is a logical reason why, maybe the game runs faster if it’s more conservative?