Have you tried Soft Cups or Diva Cups or the other similar products out there? My wife uses them and loooooves them. The up front cost is a bit but you save loads of money over time.
She also gave up shaving and has hardly ever worn makeup. Sometimes it is hard for her because she feels pressure to conform. I stopped noticing or caring a long time ago honestly. I think the more we see natural women the less we will be inclined to think anything negative about them.