What about...the occasion being the experience itself? Dressing up in something new, in a city you haven't been to in a long time. You can blend yourself in with the locals!

[ He's distracted from the side he's looking through, a thought coming to him--but a pair of pants catches his eye, and he pulls them out. ]

How about these? [ ... ] And you know, maybe you could leave your hair how it is before you tidy it. You [ uh ] you look like a whole different you in the mornings when it's like that.