4. Jude Law
The Sherlock Holmes actor has dated his fair share of women. Many of them have been Hollywood actresses, but he’s also been connected to a few catwalk stars. Law was linked to English model-turned-actress Sienna Miller from 2003-2006 and again from 2009-2011. He also dated German lingerie model Susan Hoecke in 2007, American model Kimberly Stewart in 2008, Mauritian fashion model Alicia Rountree in 2013, and he had an affair with Hungarian Playboy model Linda Zimany in 2014.
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