What: “Plus, we look good in these clothes!” bronze trophy
When: During Year Two (Rubacava)
Where: Calavera's, Lounge
Around the beginning of the second year in the Eighth Underworld, you'll find that you now own the automat and have turned it into a lounge and casino. Head down the stairs from Manny's office, then proceed further south on the first floor. You'll come out into the lounge where Glottis is playing the piano. Talk to him about leaving to find Meche and he will raise a complaint about that idea, insisting that you two should stay here. "Plus, we look good in these clothes!"
Once you've shown Glottis the VIP pass and he relocates to the High Roller's Club, I believe you've missed your chance to get this trophy.