Well

Plus

Hat

We all know about Angie's long hat-based character arc

Could use Victoria for the painter. Morgan would be fine too.

Bluh, that Sorceress Dx
Painter... little girl Maggie... Is this class a reference to Relm from Final Fantasy 6? The pixel re-release is coming out soon.
*googles Lost Ark painter*
yeah I still don't know whether this chick is supposed to be a child or not

Maybe Maggie could be the painter? Something about kids scribbling on walls?

You underestimate just how many shenanigans your fans will accept from you my good Author.

Time for a skippable cutscene where Angie explains the "why not" to Morgan.

Yeah, uh. Tentacles, paint... That awesome hat! OMG the SMOCK! Painter TentaJo is a HUGE go!

You underestimate your popularity. Anime has really made tentacles popular after all.

Dirty joke aside: If it fits well? Why not?