The 58-year-old star began her modelling career as a teenager and Cindy was soon earning more money than both of her parents.
During an appearance on the 'Kelly Corrigan Wonders: About Your Mother' podcast, Cindy shared: "I started modelling in Chicago, and in Chicago, it's a small pond, so I was the big fish pretty quickly there. And I was making more money than my parents made, more money than they could ever have dreamed of."
Despite her wealth, Cindy tries to avoid buying lavish gifts for her sisters, Chris and Danielle.
The brunette beauty fears that by being too generous, she could actually "emasculate their husbands".
Cindy explained: "If I'm giving my sister a nicer ring than her husband gives them or something like that, it just becomes this weird thing.
"I was more about giving experiences and then helping them if they need a down payment on a house or something like that. My sisters have been awesome because they always paid it back. But navigating being in that financial position where you could do a lot is tricky."
Meanwhile, Kaia Gerber, Cindy's 22-year-old daughter, previously revealed how her mum prepared her for life as a model.
The catwalk star explained how Cindy prepared her for life in the fashion industry.
During an appearance on 'The Tonight Show Starring Jimmy Fallon', Kaia shared: "I remember right before I was going to do my first-ever fashion show, she sat me down and had my whole family gather around and played me compilation videos of models falling.
"I think to be like, 'This is the worst case scenario.' And I was like, 'I didn't even know you could fall this many different ways.'"
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