Hey! Hopefully you haven't encountered a bug, there are two outfit that needs to be worn for the choices to appear, headwear and clothes, please do let me know if it still doesn't work!
I don't know if I wore the right thing but I'm still stuck in the second quest of new outfit's the second one I wore the tavern chaps alone but no choice appears and when I wore the apron with it, it appeared but when I press the button it says "As your about to ask, you realize your not putting on the right clothes to judge" i also wore the bandana