If you think about where the drain is connected (to your body!!) then you need to make sure it does not get pulled out. Think if you were laying and the dress went askew and it was in an outer pocket or fell from a pocket to the ground or something. She will need to make sure the drain(s) don't get pulled. And IMO, that means keeping them near the body and protected. Putting something else in a pocket of the garment doesn't seem like an issue to me depending on where the drain is located.
And yes, I get being sensitive about sizing. But you can explain to her that it's not about her size, it's about getting something larger than her size if that's what's going to give enough clearance for her needs.