Little's first film as head costume designer was Tony Scott's 1995 thriller Crimson Tide, which was followed by the 1999 family comedy The Prince and the Surfer, Rodrigo García's 2000 drama Things You Can Tell Just by Looking at Her and the 2001 television movie Uprising.
In 2000, director John Moore enlisted Little to be head costume designer on his first feature film, the 2001 release Behind Enemy Lines.
Other films for which Little was costume designer include The Crazies, Warm Bodies, Transcendence and Fantastic Four.
In 1993, Little married fellow costume supervisor Carlane Passman, with whom he had worked on Bugsy, Toys, The Pelican Brief and Sliver.
They continued working together during their marriage, with Passman serving as Little's assistant costume designer on The Prince and the Surfer, Things You Can Tell Just by Looking at Her, Behind Enemy Lines, Flight of the Phoenix and The Omen.