The most recommended books about cross-dressing

As a nonbinary trans guy, I grew up obsessed with novels about women disguising themselves as men. I loved everything about the trope, and always felt disappointed when they had to go back to living as women. It is a trope I eagerly embraced when I wrote Shrouded Loyalties, and though I didn’t yet know the term “transgender,” I was already exploring my own gender identity through my reading and writing of this theme. The books I’ve chosen to highlight here are ones that became some of my very favorites, and also feature action-packed wartime settings like the one used in Shrouded Loyalties.

The custom of Masquerade, of dressing as Other, has long fascinated me. In writing Star-Crossed, I set out to investigate how and why one girl might pass as a boy in an era when gender roles were sharply differentiated. I once crossed an ocean working aboard a wooden, three-masted ship – a 20th-century replica of the Bark Endeavour, circumnavigating in 1999. Sleeping in hammocks and working aloft in the rigging, I discovered this life required teamwork, stamina – and a sturdy, practical costume. Trousers, not petticoats! I have worked as a registered nurse and I earned a degree in History; these experiences combine in Star-Crossed. 

I am the author of several novels—in addition to the one featured here, Impact, It Wasn't Enough (Finalist for the Eric Hoffer Award), Exile, and What Happened to Tom (on Goodreads' "Fiction Books That Opened Your Eyes To A Social Or Political Issue" list).  I was a columnist for The Philosopher Magazine for eight years, Philosophy Now for two years, and the Ethics and Emerging Technologies website for a year ("TransGendered Courage" received 35,000 hits, making it #3 of the year, and "Ethics without Philosophers" received 34,000 hits, making it #5 of the year), and I've published a collection of think pieces titled Sexist Shit that Pisses Me Off. 

The custom of Masquerade, of dressing as Other, has long fascinated me. In writing Star-Crossed, I set out to investigate how and why one girl might pass as a boy in an era when gender roles were sharply differentiated. I once crossed an ocean working aboard a wooden, three-masted ship – a 20th-century replica of the Bark Endeavour, circumnavigating in 1999. Sleeping in hammocks and working aloft in the rigging, I discovered this life required teamwork, stamina – and a sturdy, practical costume. Trousers, not petticoats! I have worked as a registered nurse and I earned a degree in History; these experiences combine in Star-Crossed. 

Stuck at home during the pandemic, I started watching historical fiction and fell in love with the British miniseries, Hornblower. Suddenly I found myself writing my own stories about an imprisoned midshipman and Ella Parker, a surgeon that saves him. But there was a plot hole. Women could not be doctors in 19th-century England, leave alone ship surgeons. Thus, I sent Ella into medical school disguised as a man, and Hearts and Sails series was born. Looking for interesting cases for Ella to observe and treat, I became obsessed with the history of modern medicine. I also wanted my character to overcome great obstacles and eventually prove to others what a woman can do.