Born in Stamford, Connecticut, Taylor Jacobson started out as a wardrobe assistant on Gwen Stefani's Harajuku Lovers Tour, as well as a wardrobe assistant for films like The Chronicles of Narnia: The Lion, the Witch and the Wardrobe and Havana Nights. In 2005, she started working with fashion stylist Rachel Zoe and was eventually featured on the Bravo reality series The Rachel Zoe Project when the show premiered in September 2008 as Zoe's styling associate. She remained on the show until the second season as she was fired by Zoe in November 2009.