Crossing Dress Lines

Sea Change Cover - the hero has a four foot divot in his chinCross dressing is an old and familiar plot trope in romance. We’ve talked about it here before, and there’s a pretty thorough list at AAR of all the cross dressing romances they’ve cataloged.

I joke (A LOT) about how oddly easy it is for heroines to easily pass as boys. So many romance heroines years past puberty have grabbed some boys clothing, possibly from a well-hipped stable lad, I presume, and shoved a cap on their heads and presto! Everyone thinks she’s a boy.

Yet there is an amazing history of “passing women,” women who “passed” as men, often marrying other women and living publicly as males, even practicing male professions such as medicine. Cross-dressing was a favorite plot device of many a writer, including Shakespeare.

NB: I may be incorrect in my terminology here. I *thought* “passing women” referred to women who lived outwardly as men, but I’m also finding references to individuals who “passed” as another race. I’m referring here to gender and if I’m using the wrong term, I apologize. 

There are several accounts of “passing women” whose stories are jaw dropping. Murray Hall was a politician who voted long before women had the right to do so, and was not revealed to be a female until after Hall died of untreated breast cancer. Hall refused treatment because his gender would have been revealed. James Barry was a British military surgeon whose gender was also not discovered until after his death in 1865. And musician Billy Tipton was similarly revealed to be female upon his death in 1989. 

I’ve been thinking about the history of women who passed as men – and how dangerous it was for them – as I’ve been writing up questions for the book club chat for Darlene Marshall’s Sea Change. The heroine, Charlotte, is passing as a male and practicing medicine on a ship as ‘Charley.’ She’s described frequently as not very curvy, with a square jaw and somewhat plain face, but she also takes very careful steps to hide her secondary sex characteristics: she binds her breasts, for example, and she tries not to be seen without a jacket on, even in the Caribbean (oy).

This is a bit of a different type of cross-dressing heroine. Charley is living full-time as a man through much of the story, without anyone on the ship knowing her gender. Charley is in danger if her charade is found out, especially since her reputation is pretty much obliterated due to all the naked manjunk she’s seen professionally. One of the things I find really interesting about Charley is that she’s aware of the many advantages she attains by passing as a male, but she’s also aware that for every social and economic advantage, there’s an equally increased danger of violent consequences if her disguise is discovered. Charley’s uniqueness as a heroine is giving me a lot to think about.

Cross dressing heroines are often masquerading as boys for a few chapters, or maybe a few scenes or one key scene in particular, such as when Frances in Midsummer Magic dresses as a male so that she will be permitted to watch a stallion mount a mare with her husband (yes, of course, you do know what happened next). (Bow chick-a whinny snort).

The reader fascination with bending gender in romance continues. On Twitter the other night I asked about a book someone had emailed me about – the reader had read the sample and wanted to go read the rest but couldn’t remember the title. In the sample, the heroine is investigating something while disguised as a male and working as a valet to a duke. There’s a scene where the heroine shaves the hero in the bath.

The Lady's Secret - cross dressing romanceThe reader, L, remembered the book after emailing me – she had read the sample online, and the book isn’t out yet: it was Joanna Chambers’ The Lady’s Secret, [AMZ | BN] scheduled for publication on 7 November 2011.

Yet the query via Twitter revealed a few other recent cross-dressing heroines, including

Sabrina Jeffries’

(sorry) Sophie Jordan’s Sins of a Wicked Duke [AMZ | K | BN | K | WORD] which features an orphaned heroine who works in household service disguised as a male so as to avoid the unwanted attention of unsavory nobility who like to force themselves on their household staff. But of course her current employer is puzzled by his own interest in the heroine he thinks is a boy, and she’s totally got it bad for him and is trying to keep that to herself.

I think that’s one of my favorite and yet most frustrating stock moments in cross-dressing romance: when the hero gets all confused because he’s having feelings he can’t identify or control about another DUDE. Commence angst and self-recrimination or anger or something like that. The confusion of the hero questions gender in a way that I find fascinating – though the conclusion is that feelings for what the hero thinks is another man can often be labeled as “homosexual,” when really, it’s bisexuality the hero might be confronting. As Candy wrote back in 2005 about hero archetypes,

I’ve noted before that I enjoy it when taboos involving gender lines are broken, or at least bent and bashed around a bit. It’s part of the reason why I like romances involving cross-dressing. When the characters are feeling what seems, at the surface, to be a homosexual attraction? Love it. Love watching the characters struggle with it. Some people are squicked by the idea that the characters, by evincing this attraction, are not 100% hetero. Most of the people I know who are squicked by this aspect almost always say the hero is showing signs of being gay and they’re worried that he might run off with the footman, when really, he’s showing signs of being bisexual, and tendencies towards monogamy are not, as far as I know, exclusively associated with sexual orientation.
Overall, however, the underlying message is a pretty attractive one to me, even if it’s not necessarily realistic: that it’s the essence of somebody that’s attractive, and not necessarily their packaging, even something as powerful like gender.

Yes. That. Cross-dressing is as much a part of romance as it ever was, and makes for many an adventurous plot, even as heteronormative standards are often impressed upon the narrative (to wit: You’re not gay, that’s a GIRL. Aren’t you RELIEVED that you’re NOT GAY?!) (Cue me gritting my teeth.) As Candy wrote, part of what romance explores is the idea that these two individuals are attracted for reasons that go deeper than the “packaging.” That includes, sometimes, gender. There is often some distinct and unexplained element of attraction, something that makes the hero notice something special about the heroine, and vice versa, even when one or both are not what they appear. I love and am fascinated by the idea that what attracts us toward one another is not exclusive to gender (or race, or class, etc. as romance has also explored a bit) and that individually we are unique and our uniqueness is identifiable by those who care about us, even when we hide parts of who we are.

Do you like romances in which there’s cross-dressing? What are your favorites? What’s the most startling exploration of gender you’ve read in a romance?



Random Musings

Comments are Closed

  1. 1
    Melissa says:

    I have never read a cross-dressing novel that I liked. Mostly because of the whole ‘thank God I’m not gay’ vibe a lot of them have. Your point about bisexuality is an interesting one but I’ve always thought the cross-dressing trope was about the idea that the hero was so uber-masculine that they could ‘sense’ a woman (their woman?) even under layers of masculine attire and a silly swagger.

  2. 2

    I think you need to carefully distinquish between crossdressing for purely practical reasons, and being transgendered. Billy Tipton seems to me to be a clear case of a transgendered man, not a crossdressing woman, and the other cases you mention may be the same. As there is potential for much offense in discussing the topic, you should be very careful in your terminology.

    I gather crossdressing for kink purposes is very little touched on in Romancelandia?

    Good point about bisexuality. Unfortunately in too many books, the opinions seems to be that if you go gay, you never go back. And that’s probably not the case at all – look at Freddie Mercury, having many wild flings with guys but tenderly devoted and sexually attracted to a woman who ended up being a main recipient of his will.

  3. 3
    mkir says:

    I’ve read crossdressing (female as male) in romance before. I also read fanfiction, of the m/m variety mainly.

    Now I wonder: has there ever been a romance novel where the hero falls for a heroine who turns out to be a cross-dressing *male*? That does not end as a tragedy? Or is that too niche?

    (genderbending is not uncommon in fanfiction, and I often like the issues it explores. Of course, in fanfiction, it’s easier, they can just end up magically genderswitched for porn… er, plot purposes. Then again, some of the fandoms feature magic/supernatural stuff as part of their canon…)

  4. 4
    Ros says:

    It is a long-held dream of mine for there to be a film adaptation of Heyer’s The Masqueraders in which the cross-dressing is done so successfully that the audience gasp when they realise what’s happening.  I have spent many happy hours mentally casting actors who could make it work and I have decided that James McAvoy would be the perfect Robin.  I’d love to see him in a dress.

  5. 5
    Rhian says:

    Easily The Corinthian, These Old Shades and The Masqueraders by Georgette Heyer. The key point: the hero figures out that the heroine is cross-dressing very early on, if not when he first meets her. Clearly some people are able to look like the opposite sex, but I don’t tend to find it’s done very convincingly in romance novels, and I absolutely hate the “Oh no, I must be gay!/Thank goodness I’m not gay!” moments.

    The Masqueraders is probably my favourite of the three because it has both a cross-dressing man and a cross-dressing woman, and given the era (late 1740s-ish) and the hair powder and cosmetics used by both genders, it seems to make the most sense. There’s also a solid plot-based reason for the cross-dressing – something that often seems lacking. It would have been an outrageous thing to do, and absolute ruin if one was found out, so if there isn’t a very good explanation for it I don’t enjoy the book. I also dislike the “Oh woe is me, for I am not allowed to do anything as a woman” theme… the occasional remark on the subject is okay, but it almost always comes across as a modern author giving modern ideas to a historical character.

    (In other news, I’m hard to please, and I haven’t had my coffee yet!)

  6. 6
    Cassie says:

    Pam Rosenthal’s Almost a Gentleman has a great moment when the hero, realising he seems to be falling for a man (really the heroine), goes ‘Huh, that’s interesting,’ shrugs his shoulder and keeps on walking. There’s no angst at all! At least, none that I remember.

  7. 7
    kylie says:

    Probably a bit niche but Carol Queen’s The Leather Daddy and the Femme is one where there is some believable cross dressing/gender bending attractions.  That said it is categorised as erotica rather than romance, and deservedly so.

    I don’t always find it particularly believable in historicals, simply because it is often an excuse to get the heroine in clothes closer resembling modern ones, for modern reasons.  I read a bit too many nineteenth and early 20th century books as a child to find this reasonable- the heroines had other ways of accomplishing si.milar tasks without resorting to cross dressing (or at least not as often). Not quite Potato Rage, but enough to break the mood

    I find the stories of women who passed as men for significant periods of time interesting- both in the whys and in the hows.  In some ways gender was more fluid- if you presented as a man/woman and there was no one to say otherwise, that was the end of it-  unless physical evidence proved otherwise.  Now, with our computerised records and automatic data use, it is much harder to simply pass, rather than go through a complex legal chain. Your past is never truly buried.

  8. 8
    Bibliophile says:

    I have rarely read a romance novel in which cross-dressing is done convincingly, but one I remember is Jo Beverley’s My Lady Notorious, in which the hero sees through the heroine’s male disguise in about 5 seconds once he gets a good look at her, but later on he disguises himself as a woman and gets away with it (because he is pretty rather than handsome). I also found the cross-dressing in The Masqueraders convincing, because they had been doing it for a long time and had plenty of practice, and also because of the padded and pleated clothing and wigs used during that era.

    I would like to see it done convincingly in a modern novel – if anyone can recommend one, I’d appreciate it.

    Not a romance, but for a hilarious take on cross-dressing (and cross-cross-dressing) read Terry Pratchett’s Monstrous Regiment.

    In Ghost Riders, Sharyn McCrumb includes the true story of a woman, Malinda Blalock, disguising herself convincingly as a man to join her husband in the army during the American Civil War. Although not a romance novel, their story is very romantic as told in the book.

  9. 9
    JaniceG says:

    High Hearts by Rita Mae Brown is not technically a romance (although there is some romance in it) but it’s a fantastic novel about the American Civil War where, as with Ghost Riders, the lead character cross-dresses to join the Confederate Army and be with her husband. Most of the other men in the outfit, including her commanding officer, don’t know for most of the novel that she isn’t a man. (Interestingly, even after he finds out, he doesn’t expose her.)

  10. 10
    Sophie says:

    Cassie: yes I really liked that about “Almost a Gentleman”. It was fairly unheteronormative for the genre. Personally I like f/f crossdressing romances but they are very hard to find.

    Sarah: I agree with Ann Somerville that you need to be more careful to distinguish between a cis woman crossdressing for practical reasons (or because she enjoys it etc) and trans men, though with historical figures it can be hard to tell the difference.

    I tend not to enjoy Heyer, but I may have to try “The Masqueraders”.

  11. 11
    hechicera says:

    Funny you should mention it, because that very trope (hero is confused by his own apparently same-sex feelings of attraction) is one that will turn me off a book immediately. It the reason that Sea Change remains a DNF for me. Not because it has homophobic overtones (though that would certainly be period-appropriate) but because it’s so unrealistic it naggingly punctures my suspension of disbelief to a degree that takes the fun out of the read for me. The idea that feelings of attraction toward a member of the “same” sex signal, not a completely believable degree of orientation elasticity, but some sort of superhuman, subconscious estrogen-sniffing powers of deduction on the part of the hero (or his penis) just makes me roll my eyes and put the book down.

  12. 12

    Sometimes this device works for me and sometimes it doesn’t.  When it works for me it’s usually b/c the author is way inside the hero’s head.  Then again, I’m a head hopper from way back. 

    One of the best to use this device to me was Jackie Ivie’s “Lady of the Knight.” It’s a Highland romance, which I love and the heroine is out to avenge her clan.  She dresses as a lad and wields a sword better than any of the men.  It’s a great read.

    BTW loved my word/image:  “southern75”.

  13. 13
    Lisa Heermann says:

    “… The confusion of the hero questions gender in a way that I find fascinating “

    Are you questioning gender expression or sexual preference?  Until a relative of mine started the transition from from male to female, I did not know that those are 2 different topics.  In “Average-land” the overlap is so total that most people haven’t needed to know that there is a distinction to make between the two concepts.

    Also, I keep coming across articles and commentaries that – for me – support the concept of spectrum for many aspects of the human condition.  The first that I recall is the Autism spectrum.  What “chimed” for me was the speaker saying everyone falls ‘somewhere on the Autism spectrum’.

    We all manifest/express differently.  Spectrum seems to be able to describe (include!) more people.  I feel that anything that weakens “other = different = BAD” is worth supporting.

  14. 14
    snarkhunter says:

    I second Ann Somerville’s point about transgendered vs. cross-dressing. James Barry was almost certainly transgendered—though I think you are aware of this, as you used Murray Hall’s preferred gender in your discussion of him. So I’m not trying to correct you.

    I’m fascinated by the women who cross-dressed to fight in wars—the (American) Civil War, in particular, because there were so many of them. (I read a book that covered historical cases of women soldiers, and my favorite bit was the letters from their fellow soldiers that mentioned things like “Private So-and-so gave birth to a healthy boy last night, much to everyone’s surprise.”)

    I’m totally squicked by the “Oh, yay, I’m not GAY” response, but I’m still intrigued by Sea Change, and plan to read it. Though I’m not convinced by attraction being able to discern male from female, I do think that while people mostly see what they expect to see, at the same time, some people are also more observant than others. In which case it may be obvious that a person might be more than he or she seems to be.

    Also, I want to see more heroes cross-dressing. What’s up with that gap?

  15. 15
    Tam says:

    I usually really dislike this trope, but I quite liked the way Eloisa James did it in ‘Duchess by Night’ (which surprised me again because up until that book, Harriet had been my least-favourite duchess).  I think it was the sense of playfulness in the book, and the way Harriet’s horizons expanded as her skirts narrowed to breeches.

  16. 16
    Janey Chapel says:

    I developed this particular little kink as a teenager when I read a Harlequin Presents by Mary Wibberly called Gold to Remember. In that book, “Jan” is in contemporary South America and dresses as a boy to keep tavern patrons from getting all up in her hooha. The friendly neighborhood priest arranges a ride for her to someplace more civilized with Luke Tallon, the hero. He’s attracted to her, naturally, and maybe it’s my rose-colored-glasses read on it, but he seems truly appalled at the idea that he’d be attracted to a *young teenager* but less appalled that the teenager in question is a *boy*. “I thought I was…,” he says. Of course then he ruins it by saying he thought there was something wrong with him, but I’m chalking that up to the age difference more than the gender… and the fact that the book is probably from the early 1980s. Pretty edgy for Harlequin at the time!

  17. 17
    June says:

    One of my favorite books from years ago was called “To Touch The Sun” by Barbara Leigh.  I think it was a Harlequin Historical.  It was the first book I had read where the girl disguised herself as a boy with any believability.  It was set in Medieval times and she starts her “life as a boy” at a young age after fleeing attack on the family castle. 

    She trains as a knight with her brother and is better at it than he.  Her whole life and identity is in being a knight.  She defeats the hero in battle and makes him her prisoner and they become friends.  When he realizes he’s attracted to her/him he is wracked by guilt (because of his religious beliefs) but eventually decides—before learning the truth—that he is willing to sacrifice everything to be with her/him.  For the time (1991-ish), it went against a lot of tropes.  Including the fact that she preferred being a “man” and didn’t change her mind about that.  Or want to have babies with the hero.

  18. 18
    sugarless says:

    I can see where people are getting squicked out by the whole sense of relief surrounding not being gay, but you do have to think, particularly given the time periods most of these are taking place, it would be a relief not to be gay. Even if the heroes themselves are enlightened far beyond their contemporaries and have no problem with homosexuality, it would be a difficult life.

    I’m not saying that a homophobic hero wouldn’t turn me off, because it totally would, but I can understand a sense of relief at the prospect that he wouldn’t have to choose between taking a wife and living his life as a lie or being utterly reviled by society.

    Anyway, for that reason, the big “Oh, thank god I’m not teh GAY” scene doesn’t really bother me that much. I support gay marriage, I celebrated right alongside my friends, both gay and not, at the repeal of DADT, but if I were in a historical romance and thought I was gay, I would probably be somewhat relieved as well when it turned out I wasn’t.

    In any event – I’ve actually only ready a small handful (har) of romances that had the cross dressing theme, so I’ll have to check some of these out. And Candy was right; there’s something extremely attractive about the idea, true or not, that it’s someone’s essence that your hero is attracted to, rather than anything tangible.

  19. 19
    Cakes says:

    What I like so much about the cross dressing trope in historicals is that it gives women a real freedom that they hadn’t known. Yes, there are some that grew up with brothers and rode horses in breeches growing up, but the ones that experience the freedom that losing the iron maiden of female fashion and societal prisons that surround them are so much fun to watch as they experience this whole new world open to them.

  20. 20
    mochabean says:

    Check out The Beacon at Alexandria by Gillian Bradshaw. This is one from the mid-80s, and not technically a romance, but it used its historical setting (late Roman empire) to deal deftly with the sometimes problematic issue which is too often solved by the hero’s mighty wang detecting the heroine’s disguise to show “thank god he’ s not gay.” (ugh) The story is about an Ephesian noblewoman who dreams of practicing medicine.  When her father arranges an intolerable marriage, she runs away to Alexandria, disguised as a eunuch, and learns her chosen profession.  Many adventures ensue: she’s apprenticed to a dedicated Jewish physician, becomes the personal physician of the archbishop of Alexandria (the book includes a pretty fascinating look at early Christian struggles between church and state),  then works as a military doctor on the northern frontier.  Her love interest is a good friend who, while not inclined that way himself, is much more matter-of-fact about same-sex attraction, given the time in which the book is set, so there isn’t that “oh nos, gay people, horrors!” set up to deal with.  The romance is really secondary to the historical fiction (and very chaste), but it is a wonderful novel.

  21. 21

    One of the things that intrigued me when researching Sea Change was the number of women serving in the Royal Navy who were allowed to keep serving after their identities were revealed.  A prudent captain knew the value of a qualified topman, regardless of gender, vs. some tailor grabbed by a press gang.

  22. 22

    I did enjoy the cross dressing Heyers, but other than that, no other x-dressing romances stick with me. However, I did read a book I loved, historical fiction by Patricia Dunker about James Miranda Barry (title The Doctor in the US).

    It was a terrific novel.

    In the churchyard of one of the main brighton churches, where I used to live before coming to Brussels, was the gravestone Of phoebe Hessel, who served for 17 years during the 18th century in the army as a man. She’s on Wikipedia.

    Viola is my favourite cross dressing girl.

  23. 23
    Carin says:

    What sugarless said a few posts abover me – that sums up my feelings on it.

    I think Alanna by Tamora Pierce was the very first book I read featuring cross dressing and I was enthralled. It’s a children’s book, or maybe YA? about a girl who dresses as a boy so she can become a knight.  I still really like to read this trope in romance when it focuses on the h/h coming to care for each other and appreciate each other in ways they probably couldn’t have done as as a man and woman.

  24. 24
    Barb in Maryland says:

    Well, my two faves have already been mentioned—The Masqueraders and The Beacon at Alexandria
    In Amanda Quick’s Victorian era Arcane Society books she features several women who live outwardly as men.  They even have their own upscale gathering haven-The Janus Club-modeled very firmly on the men’s clubs.

    And thanks to @sugarless for a good take on the hero’s relief of finding out he’s not gay.

    spamword others 75.  I am sure there are at least 75 other books that feature this trope.

  25. 25
    RachelT says:

    I love this trope. The Masqueraders was my favourite Georgette Heyer since teenage years and it stood up to a recent re-read. I really liked the laid back attitude of the hero in Pam Rosenthal’s Almost a Gentleman.
    A recent book I have enjoyed is Showdown at Yellowstone River by Angelia Sparrow and Naomi Brooks:

    Gunslinger Matt Court has hung it up for good after a disastrous encounter in El Paso. He moved to Dakota Territory, took out a homestead and started courting Annie, the banker’s daughter. But when Annie comes up pregnant and runs away with her lover, her father calls in the notorious killer, Paz, to eliminate Matt. But the mysterious Paz holds many secrets and Matt discovers not only the gunfighter’s personal code of honor, but a truth that is worth both their lives

  26. 26
    Sierra says:

    There’s actually an article over at about people who lived their lives as the opposite gender. I’m not sure about the accuracy of all of it, but it’s definitely interesting and entertaining.

    The only romance with cross-dressing that I remember right now was in an SEP historical novel, which I can’t think of the name of right now. It was brief cross-dressing, and I think the only reason the girl fooled the guy was because he didn’t look at her that closely. Granted, she was just cross-dressing so that she could get close enough to kill him, so…it’s not like she was wanting to spend too much time with him.

  27. 27
    MD says:

    Not really a romance, but one of my favourite scenes from Lois McMaster Bujold “Barrayar” is this conversation between the villain and the heroine. He is trying to cause trouble between her and her husband (quoted through

    “One corner of his mouth crooked up, then the quirk vanished in a thoughtful pursing of his lips. “He’s bisexual, you know.” He took a delicate sip of his wine.
    “Was bisexual,” she corrected absently, looking fondly across the room. “Now he’s monogamous.”
    Vordarian choked, sputtering.”

    I found this quite romantic, actually.

  28. 28
    Beans says:

    Johanna Lindsay had a novel with a woman passing as a man.  A girl who was orphaned at a very young age lived as a boy in an Oliver Twist-style environment, because if she was a boy she could be a pickpocket but if she was a girl, people would try to force her into prostitution, I think?  Anyway, she had lived as a man for most of her life by the time the novel starts.  It was one of the Malory ones, I think.  And they got around the “hero being confused by apparent homoerotic feelings” by having the hero figure out right away that she’s a woman even though she had been living as a man for how many years and no one had figured it out yet!

  29. 29
    Katie D. says:

    “A Difficult Disguise” by Michelle Kasey (aka Kasey Michaels) which I’m pretty sure was a HABO back in the day. There is definite questioning of gender attraction, and this was a Signet Regency Romance from 1990!

  30. 30
    snarkhunter says:

    Not really a romance, per se, but right now my favorite cross-dressing books are Scott Westerfeld’s Leviathan novels. Derwyn/Dylan is totally believable as a girl dressed as a boy, in part because she’s a teenager playing a teenager, and she has to work at being a boy. What’s more, her love interest, himself a teenager, really doesn’t see through her disguise. He likes Dylan immensely—they’re best friends. He doesn’t know that Derwyn is in love with him. (YET. DO NOT SPOIL ME FOR GOLIATH.)

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