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This is the standard academic treatment of cross dressing by two scholars who have been researching sex and gender for several decades. 

Also worth looking at is their edited collection: 
Bonnie Bullough, Vern L. Bullough, and James Elias (eds.) Gender Blending: Transvestitism (Cross-Dressing), Gender Heresy, Androgyny, Religion & the Cross-Dresser, Transgender Healthcare, Free Expression . . . 

and also Bert & Lori: The Autobiography of a Crossdresser by Robert J. Rowe and Vern L. Bullough.

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One of my favorite authors explores transexualism, covering both male-to-female and female-to-male transsexuals. The book is based on numerous interviews with transgendered individuals and their partners. Her discuss ranges from early transgender pioneers such as Christine Jorgenson and Renee Richards to some of the growing number of female to male transsexuals of the last decade. There's a good bibliography, and a rather good recounting of the clinical history of transexualism. Always provocative, Califia is at her best when she's fighting for a cause, and this is a cause she deeply believes in. Califia has been fighting for the rights of the transgendered for more than a decades now, and has been instrumental in getting them accepted within the gay and lesbian community. 

In this book, Garber (Ph.D. Harvard) explores transvestitism and transsexuality and the larger culture's problem accepting it. This is a dense book, rooted in literary theory and deconstruction, but her points are fascinating, though a bit overstated. She argues that gender is culturally constructed and sees the cross-dresser as a third gender in a neutral position between male and female--a position that has played an essential role in the development of western civilization. 

If you're looking for fashion advice for the cross-dresser, Joann Robert's two volume set is virtually all that is out there. The first volume covers make-up and hairstyle, the second covers how to dress to pull off the masquerade. Roberts has also written one of the better books aimed at helping spouses cope with their cross-dressing partners.

Joann Roberts, Coping With Crossdressing (Creative Design Services, 1991), $12.00

Joann Roberts, Art and Illusion: A Guide to Crossdressing, Vol. 1, Face & Hair

Joann Roberts, Art and Illusion: A Guide to Crossdressing, Vol. 2, Fashion & Style (1994)

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Rudd, is on the Board of Directors of Tri-Ess and holds a doctorate in Cultural Studies and Psychology. This is her first book on cross dressing and explores how she came to terms with her husband's cross dressing. Her primary audience for the books are the wives and girlfriends of male cross dressers, and in the book she debunks many of the myths associated with crossdressing such as that all crossdressers are gay. It is a good book to give a spouse who is struggling to understand your predilection for the other gender's clothes. 

Rudd has also written three other books on crossdressing: 

Crossdressers : And Those Who Share Their Lives which offers the pictures and stories of fifty crossdressers and their wives; Crossdressing With Dignity : The Case for Transcending Gender Lines which picks up where her first book left off; and Who's Really from Venus? : The Tale of Two Genders which is takeoff on the similarly titled popular self-help book. 
 
 

Porn star turned sex activist, Vera founded the world's first training academy for cross dressers in 1992 in New York. This book actually has as much to say about Vera's school, her clients (about 100 per a year), and her personal perspective and approach on cross dressing as it does about the practical how-to of effective and believable cross dressing. Her emphasis seems a bit more toward high camp than some cross dressers might like. There is plenty of material for sissy maids and similar bdsm feminazation and role-playing. Vera offers advice on finding one's femme self, speaking like a woman, etiquette, cosmetics, walking in high heels and more. It includes photographs and stories of several of her graduates.