Photo Set Number 1

Matt Weinberg, as crossdressing Booger Spencer,
from the film The Hot Chick, 2002

Aidan Mitchell as crossdressing Sam Malloy,
from the television series "The Riches," 2007

John Leguizamo as a female impersonator,
from the film To Wong Foo, Thanks for Everything! Julie Newmar, 1995

Chris, her husband Jennifer, and their two children. Jennifer, who used to be Jeff,
decided to live as a woman. Chris has no intention of leaving her husband.
From the documentary My Unique Family: "That Woman is My Husband"

Aidan Mitchell as crossdressing Sam Malloy, from the television series "The Riches," 2007

Fictional members of the Vienna Boys Choir perform in a show at their school,
from the film Almost Angels, 1962

Billy's best pal, who likes to crossdress at home,
from the film Billy Elliot, 2000

Actress Kate Hudson, out on the town with her son, Ryder

Anonymous crossdresser

Korean pop singers in male and female guise.

Portrait of a boy from the early twentieth century,
when dresses and girlish hair styles were customary for young boys.

Chad Lowe, as Stephen/Stephanie,
from the film Nobody's Perfect, 1989

Portrait of a brother and sister, from the early twentieth century,
when young boys often wore dresses for casual and formal occasions.

Eric Reiley McClendon, who performs the roles
of a twin brother and sister in the episode "Identity," from the television series "Law & Order: SVU."

Anonymous Japanese cosplayer.

Jennifer Williamson and Curtis Williams,
from the film Silk Seduction, 2006

Harland Williams, Barry Watson, and Michael Rosenbaum,
from the film Sorority Boys, 2002

Alex D. Linz, as crossdressing Bruno,
from the film The Dress Code, 2000

Anonymous little boy playing ballerina

Bill's New Frock

Pics from three different versions of the film-adaptation of the novel by Anne Fine.