Another entry in my Week of Imaginary Boyfriends/Girlfriends! Today I present to you: Alanna of Trebond and Olau, a.k.a. The Woman Who Rides Like A Man.
I have categorized Robin Hood and Gilbert Blythe as broader Types I fall for (The Rogue, The Perfect Man), and Alanna is certainly indicative of a sort of girl I tend to crush on in books: The Cross-Dresser. But first! Let us discuss the awesome that is Alanna of Trebond.
I was first introduced to the land of Tortall through Tamora Pierce’s IMMORTALS books because Daine, the protagonist, has the ability to speak with animals. The power to speak with animals is only the superpower I coveted most as a child. In these books there was an alluring figure named Sir Alanna, who was the King’s Champion knight and a woman to boot. Alanna in THE IMMORTALS books is somewhat disappointingly conventional-ish, but nonetheless, I was intrigued enough to pick up the LIONESS books.
And fell head over heels in love.
She is strong, blunt, and not terribly feminine, qualities I admired because I recognized them in myself. But more than that, what was interesting to me about Alanna was her life as a boy and the liminal space she would grow to inhabit and eventually become comfortable with. There have been other cross-dressing heroines in fiction (most notably in Shakespearean plays), but Alanna stood out because in the end she chooses to live in that liminal space instead of succumbing to heteronormative ideas (well…sorta) like Viola and Rosalind did, or choosing to become an actual man.
I have always been attracted to the boyish femme, or the Apollonian androgyne, as Camille Paglia would dub her. It’s the sexual persona I am most comfortable with and the most comfortable being. It’s funny because Alanna embodies many of the traits of the Kickass Heroine I so despise, but in her, I find it endearing. Is she the best swordsman in the land? Check. The bestest knight? Check. Yet, despite all this, I think it’s because Alanna never really does this to prove a point, or at least, that’s not how I feel when I read it. Does she mention several times that women can do these things too? Absolutely. But in her case, she had ALWAYS been predisposed to be pugnacious and physical, and in her world, those things happen to be considered masculine. Alanna doesn’t become a knight to prove that women can be knights too; she becomes a knight because she needs too.
Gender is a curious thing. I am cisgendered in that I am comfortable with my gender identity. Yet, femininity is something I find that’s a bit of a performance. I am girly, sure, but when I go girly, I go all out. I go to the place where femininity is a performance and becomes campy. It’s why I have such rapport with drag queens; we both understand idealize the performance of feminine glamor.
In my mind, this is related to girls who cross-dress in fiction, girls who recognize the performance aspect of femininity and reject it. Not that Alanna vocalizes this in as many words, but she does wrestle with the “all warrior or all woman” question a few times before coming to terms with this. I like cross-dressers who cross-dress because there is something in her that needs to present itself as male, not girls who cross-dress because it’s like…some sort of rite of passage or she needs to hide how hot she is or something ridiculous like that.
It isn’t necessarily bravery or proving a point (although a point may be proven along the way). Other cross-dressers on whom I have had crushes: Deryn Sharp from Scott Westerfeld’s LEVIATHAN books (god, I love her) and Kitty Butler from Sarah Waters’ TIPPING THE VELVET.
So that’s it! I love me some girls in boy’s clothing. What about you?

Hmm, I think this is an area where we deviate. I like non-feminine girl characters, but wearing men’s clothes isn’t an automatic Yes for me.
On a related note, have you ever watched the anime Fushigi Yugi? (It’s amazing.) That series has a cross-dressing character that I LOVE, Nuriko. But (SPOILER ALERT) Nuriko went the other direction: he dressed like a she.
I read the manga, so I am familiar with Nuriko. :)
Wearing men’s clothes isn’t an automatic yes. It’s that said girl dresses as a man and somehow lives the performative aspect of masculinity. Sort of like how drag queens are exaggerated women; I like it when girls occupy the gender space usually given to men. It usually comes out in the clothes they wear, but not always.
And Viola and Rosalind are cross-dressers, but they are still GIRLS. When it is no longer necessary, they doff their masculine clothes and live as women. The girls I love in fiction do not.