Caitlyn Jenner – $5 Million

Of course, Caitlyn Jenner will make it to the list. She just spent a whopping $5 million of her investment money to change her appearance to what it looks like today.

The former Olympic athlete and father of the Jenner twins decided to come out and tell the world who she really is in 2016. Her revelation that she was a trans woman shocked the world, but Jenner continued her transition by hiring a trusted plastic surgeon. Her initial step to her transformation was a full-face surgery to help her achieve a feminine face. It includes reshaping her jaws, chin, and nose. Additionally, she also removed her beard and reconstruct her hairline. Caitlyn’s second procedure was breast implants, which made her body look more curvy. That is not the end of her quest, though. Caitlyn went under the knife again for gender reassignment, which she says completely transitioned her and erased the last bit of her former self.