Holbrook was discovered while working part-time as a carpenter for a theatre in Kentucky. He signed with Elite Models in 2001. He has worked for other agencies such as Wilhelmina Models.
Holbrook has been a model for such designers and labels as Gucci, Jean Paul Gaultier, Versus, Hugo Boss, Bill Blass, Calvin Klein, Moschino, Marc Jacobs, DSquared².
Holbrook is also a photographer who has done work for David Armstrong. He is also a sculptor, and exhibited his work in his first art show, "Iscariot", in RARE gallery in Chelsea, New York from April 19 to May 17, 2008.
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