Collection of items relating to the American actor's December 2006 cover shoot for Vanity Fair, including a pair of white Calvin Klein briefs (size 32), a group of three prosthetic tears, an original copy of the December 2006 edition of Vanity Fair, and a highly amusing typed letter of provenance and associated color documents. 

The present trunks were worn by Brad Pitt for a Robert Wilson video shoot depicting Brad Pitt firing a water pistol in a downpour. The shoot took place shortly after Pitt's return from Italy and filming for the hit film Mr & Mrs Smith with Angelina Jolie. The use of the image on the Vanity Fair cover a year later was a controversial one, as it was allegedly not in Brad Pitt's contract for the shoot.

Acquired directly from Brad Pitt at Rocky Mountain Studios in Hollywood in 2005 and sold together with a detailed letter of provenance.