Isabella Calthorpe (Married To Sam Branson)

To be fair, this English rose (full name Isabella Amaryllis Charlotte Anstruther-Gough-Calthorpe) wasn't really "starting from the bottom" when she wed Sam Branson, son of Virgin billionaire Richard Branson, in 2013. The socialite and minor actress, who now has two Branson children with ridiculous names of their own, has always run in royal circles; her mother is a Lady with a capital "L," she herself is friends with Prince William, and she's the half sister of Prince Harry's ex, Cressida Bonas. We will say, for a British blue blood, Isabella is exceptionally outdoorsy - Sam regularly shares photos of their adventures, from hikes to kayaking to weird spiritual retreats in Bali.

[Photo via @bransonsam]

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