Hope Dworaczyk
Long before marrying Robert F. Smith, billionaire founder of Vista Equity Partners, Hope made a name for herself. After graduating high school, she wont Miss Texas. Then, she became famous as a Playboy model. In fact, she won Playmate of the year during her time modeling. Despite the 22 year age gap, the two married in 2015 and have a son Hendrix together.

Hope Dworaczyk
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Elle Macpherson
Real estate billionaire Jeffrey Soffer married this Australian model in 2013. Actually, Elle Macpherson, who has been on the cover of the swimsuit edition of Sports Illustrated five times, was engaged to someone else when the two met. Now, they have two children together. Sadly, the couple split in June 2017.

Elle Macpherson