Well, this drawing sort of turned out like shit but I figured I'd post it anyways. The drawing felt uninspired but the idea behind the drawing is something I had a dream about a long time ago.
I'm not sure your feelings on the idea of the his/Hers types of matching stuff. Sometimes you'll see towels/robes set up in that way, other times you'll find some outfits designed to match except be tailored to each gender. In other cases you'll find the mother/daughter "mini-me" type matching outfits as well.
Why not a his/Hers sissy/Mistress outfits?