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A Guide to Perfecting Femininity: Virginia Prince’s “How to Be a Woman Though Male”

This post was written by Tayler Fane, a recipient of an Archival Scholar Research Award for the 2022 Spring Semester.

“[By embracing your femmeself], you will…put yourself that much nearer the future—not a time when all men will wear skirts, they are only symbols, but a time when the polarization of our present culture will have been vastly modified; to a time when all people—males and females alike—will be able to express their reactions to a given environmental or emotional situation by whatever means and mechanisms seem appropriate and satisfying to them at the moment” (Prince 117).

(Above) Author photograph of Virginia Prince, featured in How To Be a Woman Though Male, 1987. 

Virginia Prince (1912-2009) was a self-proclaimed “transgenderist” educator and activist who dedicated her time to providing information for heterosexual crossdressers. As the founder of Transvestia, a magazine dedicated to creating a social and educational resource for crossdressers to communicate and share their stories, Prince helped create a sense of belonging within the crossdressing community for 20 years. Prince also founded the Alpha Chapter of the Foundation for Full Personality Expression (FPE) which became the Society for the Second Self, or Tri Ess, in 1975.

(Above) Cover of How To Be a Woman Though Male, 1987.

At 55, Virginia Prince began living as a woman full-time. A few years after transitioning, Prince first published her influential book How To Be a Woman Though Male in 1971. Archives & Special Collections at the University of Pittsburgh Libraries holds an edition of the 6th printing from 1987. This book acted as a guide for heterosexual crossdressers, providing information on the physical, cosmetic, and aesthetic elements of fully embracing one’s feminine self and how to successfully pass as a “real” woman. 

The book is split into 14 chapters. The first 11 give readers tips and tricks on how to dress, accessorize and behave in manners that emphasize one’s feminine traits and suppress one’s masculine traits. While Prince did not believe that crossdressing required one to abandon their masculine traits completely, she did believe that the goal of crossdressing was to be as good looking a woman as possible, which requires careful attention to the details that help flatter and femininize one’s appearance to create a realistic transformation.

(Above) “Useful Hair Styles I” illustration on page 38 of How To Be a Woman Though Male, 1987.

(Above) “Size charts” on page 83 of How To Be a Woman Though Male, 1987.

In the last three chapters of How To Be a Woman Though Male, Prince provides her insight on the distinction between sex and gender and the difference between transgender and transsexual identities. While transgender and transsexual essentially mean the same thing today, these two terms represented two different experiences of transness in the 60s, 70s, and 80s. Prince believed that a little boy’s desire to “be a girl” was not the same as the desire to “be a female,” and that the distinction between the two was crucial to fully understanding transgender and transsexual identities. Prince argued that most individuals who found themselves longing to transition only wanted to adopt the gender, or patterns of behavior and social roles, of their counterparts, and that sex was rarely considered or acknowledged in these feelings. Because of this, Prince argued that most folks could satisfy these feelings by simply crossdressing or learning to live as a woman full-time and that surgeries to affirm one’s gender was often misguided and unnecessary to transition.

While some of Virginia Prince’s views of the trans community do not reflect what we believe and know today, her works provided crucial information that helped pioneer trans research and community building. Prince’s activism and dedication to her community is the blueprint for how embracing one’s identity also entails giving back to your community and helping others reach that same sense of self-love and acceptance. Prince book How To Be a Woman Though Male as well as issues of her magazine Transvestia can be found at the Archives & Special Collections at the University of Pittsburgh.

Works Cited

Prince, Virginia. How To Be a Woman Though Male. Chevalier Publications, 1987.

“Virginia Prince & Transvestia.” University of Victoria, https://www.uvic.ca/transgenderarchives/collections/virgina-prince/index.php.