>>55918977Ash-Serena, Florges-Serena, and Fennekin-Serena.
Runner-ups: Journeys-Serena, Rhyhorn-Racing-Serena (which is the same outfit as Jogging-Serena btw), and Hipster-Serena.
I do like Graduation-Serena and Doridori-Band-Serena too, though, the latter of which I would've loved to see in an actual episode.