Tinsley earned A-list social status the old-fashioned way-relentless self-promotion. After briefly working at Vogue, attending Parsons for four months, and working at PR firm Harrison & Shriftman, in 2002 she gave up on the notion of a day job when she tied the knot with longtime boyfriend Topper (otherwise known as Robert Livingston Mortimer) and focused her energies on rising to the top of the social ladder. At her peak in the mid-aughts, with her comings and goings constantly featured on Page Six, Mortimer landed luxury brand endorsements, "designing" gigs, and her own reality show on the CW network. The blitz of exposure has brought with it the inevitable backlash, and in 2008 she and Topper separated. [Image via Getty]