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(written from a Production point of view)
Caballero was an advanced student in the Master of Fine Arts Costume Design Program of DePaul University in Chicago, Illinois. She has designed costumes for productions of such plays as The Crucible, A Summer's Day, and Macbeth. In the late 1990s she was the resident costume designer for the Steppenwolf Theatre Company's New Plays Lab. 
She began her Hollywood costuming career as an assistant costume designer on the daytime soap opera The Young and the Restless from 1999 through 2002. In 2001, she began working as a costumer on the television series Felicity, which was created by J.J. Abrams, the director and producer of 2009's Star Trek. Later that year, Caballero began working as a key costumer on the NBC series Crossing Jordan, which starred Miguel Ferrer. Caballero continued working on this series through 2006, after which she began working on the popular NBC series Heroes, starring the likes of Zachary Quinto, Cristine Rose, and George Takei.
Caballero's first feature film experience was as a costumer on the 2002 Paramount Pictures comedy, Orange County (featuring George Murdock). She then worked as an assistant costume designer on the 2005 comedy Monster-in-Law and as a costumer on Paramount's 2007 comedy, The Heartbreak Kid (featuring cinematography by Matthew F. Leonetti). More recently, Caballero was assistant costume designer for the 2008 films Speed Racer (featuring music by Michael Giacchino) and Hancock.