41 Super-Hot Butches and Tomboys of the Early 20th Century

There’s no day like today to cast our eyes upon some hot butch women and tomboys and otherwise-identified human beings who are unfortunately dead, but fortunately looked good and (in most cases) did cool shit while they still roamed the fields and valleys of this scorched earth. Before Ruby Rose was even a glimmer in her parents’ eyes, these people were putting on their top hats and/or trousers and giving the ladies something to whisper about in their journals.

Please note that not everybody in this was a lesbian or bisexual. Nor is everybody on this list a certified masc-of-center, butch or tomboy identified woman. (Although I was inspired to make this list while working on my second edition of Lesbian Power Couples From History, so look forward to learning more about some of these folks very soon!) Some of the women included herein didn’t typically dress “masculine-of-center” or exude a “butch vibe” but did for the picture I have included. Back in the day, women obviously had much less freedom regarding what they wore and how they presented, so it’s not always clear from archival photographs what anybody’s “authentic” gender presentation was.

I have included an asterisk before the names of the women who I’m pretty damn sure were lesbian, bisexual, or otherwise into the ladies. This is important in case any of you are into dating ghosts, which makes about as much sense as anything else these days, you know?


*Ella Wesner (1851-1917)

Vaudeville Entertainer / Male Impersonator

Wesner’s popular stage routine included plucky monologues that imparted advice to male audience members on how to treat and/or seduce a lady.


Vesta Tilley (1864-1952)

English Music Hall Performer, Male Impersonator

Vesta made her debut playing a male role onstage at the age of six, by which point her father, a successful performer himself, had already gifted her the custom-tailored suit she’d begged for as a child.


*Maude Adams (1872-1953)

American Actress

Adams is best known for playing Peter Pan on Broadway.


*Cicely Hamilton (1872-1952)

English Actress, Writer, Journalist, Suffragist


*Romaine Brooks (1874-1970)

American painter

Romaine Brooks is best-known for her paintings of women in androgynous or “masculine” attire.


Ella Shields (1879-1952)

Vaudeville Performer, Music Hall Singer, Male Impersonator


Hetty King (1883-1972)

Entertainer/Male Impersonator

Hetty King was an asshole to her lesbian fans, telling an interviewer that she was “sickened” by letters she got from women in which “they declare that they can’t eat or sleep or are going to kill themselves for the love of me.”


Lillyn Brown (1885-1969)

African-American/Native American Singer, Vaudeville Entertainer, Teacher and Actress


*Agnes Smedley 1892-1950

American Journalist, Novelist, Activist & Socialist


*Mercedes De Acosta (1893-1968)

Writer, Lover to the Stars


Selika Lazevski (1890s – Unknown)

African Princess / 19th Century High Society Equestrian


*Beatrice Lillie (1894 – 1989)

Canadian-born British actress, Singer and Comedic Performer

Bea Lillie


*Moms Mabley (1894-1975)

American Standup Comedian

Mabley wore housedresses onstage, but in her off-time she presented butch, in tailored suits.


Kitty Doner (1895-1988)

American Actress and Producer

Kitty’s parents were performers, too, and thus Kitty began performing onstage in male attire while she was a very young girl.


*Alice DeLamar (1895-1983)

American Heiress

When her father died in 1918, DeLamar inherited $10 million, giving her the title of “richest bachelor girl.”


*Nobuko Yoshiya (1896-1973)

Japanese Writer


*Ethel Waters (1896-1977)

American Singer and Actress


*Hope Williams (1897 – 1992)

American Actress


*Dorothy Arzner (1897 – 1979)

American Film Director

Arzner was the only female film director working during her era, which was a tenuous position to be in — it’s why she wore dresses and skirts to work instead of the pants she wanted to wear.


*Eva Le Gallienne (1899-1991)

British-born American Stage Actress


*Marion Barbara “Joe” Carstairs (1900 -1993)

Wealthy British Powerboat Racer

Carstairs wore men’s clothing, covered her arms in tattoos, drove ambulances during World War I, and, in the 1920s, started a womens-only car-hire and chauffering service staffed by women she met working during the war.


*Thelma Wood (1901-1970)

American Sculptor


*Marlene Dietrich (1901-1992)

German-American Actress and Singer


*Greta Garbo (1905 – 1990)

Swedish-born American Film Actress

Her 1933 film Queen Christina won critical acclaim and slayed at the box office, but censors were disturbed by a scene in which Garbo dressed like a man in order to kiss a woman she wanted to kiss.


*Anna May Wong (1905-1961)

Chinese-American Movie Star


*Valentine Ackland (1906-1969)

English Poet

Born “Mary” and nicknamed “Molly,” Valentine’s father raised her like a son, and as an adult, she cut her hair short, wore men’s clothing, and adopted an androgynous name in order to be taken seriously as a poet.


*Josephine Baker (1906-1975)

American Entertainer, Activist and French Resistance Agent of African and Native American descent


*Louisa D’Andelot Carpenter (1907-1976)

DuPont Heiress


*Gladys Bentley (1907 – 1960)

American Blues Singer, Pianist and Entertainer

At Harry Hansberry’s Clam House, Bentley performed in her signature tuxedo and top hat, sang racy versions of popular songs in a gravely deep voice, and flirted with ladies in the audience.


*Katharine Hepburn (1907-2003)

American Actress


*Frida Kahlo (1907 – 1954)

Mexican Painter


*Annemarie Schwarzenbach (1908-1942)

Swiss Writer, Journalist, Photographer and Traveler

Sidenote, this woman is a fashion icon and I am obsessed with her.


*Tiny Davis (1909-1994)

American jazz Trumpeter and Vocalist


*Beverly Shaw (1910-1990)

Nightclub Singer

The successful torch singer / male impersonator bought her own club in North Hollywood, called Club Laurel, which succeeded as a popular upscale gay night spot for 14 years.


*Babe Didrikson Zaharias (1911-1956)

American Athlete (golf, basketball, baseball, track & field), Olympic gold medalist

In addition to excelling at athletics, Babe was a fantastic seamstress who made her own golfing outfits and won the sewing championship at the Texas State Fair.


*Esther Eng (1914-1970)

Chinese-American Film Director


*Stormé DeLarverie (1920-2014)

Bouncer, Drag King, MC, Civil Rights Icon, Entertainer

Riese is a Jewish lesbian and the 37-year-old CEO, CFO and Editor-in-Chief of Autostraddle.com as well as an award-winning writer, blogger, fictionist, copywriter, video-maker, low-key power lesbian and aspiring cyber-performance artist who grew up in Michigan, lost her mind in New York and then headed West. Her work has appeared in nine books including "The Bigger the Better The Tighter The Sweater: 21 Funny Women on Beauty, Body Image & Other Hazards Of Being Female," magazines including Marie Claire and Curve, and all over the web including Nylon, Queerty, Nerve, Bitch, Emily Books and Jezebel. She had a very popular personal blog once upon a time, and then she recapped The L Word, and then she had the idea to make this place, and now here we all are! In 2016, she was nominated for a GLAAD Award for Outstanding Digital Journalism. Follow her on twitter and instagram.

Riese has written 2596 articles for us.

76 Comments

  1. Unf! So good!

    The next time I want to avoid some social obligation I’m going to use the excuse that I can’t go because I’m waiting for the second edition of Lesbian Power Couples From History. This is not some kind of slight, I’m literally camping on my sofa until I can pore over more images of vintage lesbos with commentary on their historical significance.

    Also, because my wife is reading this book right now and therefore this image is in my face a lot, may I propose Tove Jansson for the above list?

    Also, I’ve casually been accumulating images of queer women of history with their dogs because I think this is an important thing.

  2. Thoughts as I scroll down, trying to decide which is my favourite:

    Vesta Tilley didn’t get an asterisk, but there’s far too much swagger in that photo for that girl to be straight.

    Selika Lazevski looks like she’s ready to give someone a good spanking with that riding crop. *fans self*

    Hope Williams is the ethereal tender butch of my dreams.

    Picturing Thelma Woods fixing me with that brooding stare while she slowly unwinds the silk scarf around her neck.

    …And then the Katharine Hepburn/Frida Kahlo one-two punch knocked me out.

  3. Crushing here in my little corner over Katharine Hepburn and Annemarie Schwarzenbach also Tove Jansson. Swoon…
    There is quite interesting movie about Annemarie: The Journey to Kafiristan.

  4. I’ve been scrolling up and down, up and down for the last 10 minutes. I love the look on Kathryn Hepburn’s face. And Thelma Waters’ intense stare. And Ethel Wood’s smile. And Nobuko Yoshiya’s resting bitch face. Everyone on this list is smoking hot.

  5. SWOON. Joe Carstairs. Esther Eng. Annemarie Schwartzenbach. Anna May Wong. KITTY DONER. That newsboy cap and three-piece suit is killing me. I have a type and that type is everyone on this list. 11/10 would hopelessly crush on / be completely ignored by all of these incredible butches

  6. I would pay money for something that would give me an excuse to look at these photos more often. Calendar? Playing cards? Trading cards? Poster set? Coffee table book? Post cards? Also the power couples.

    • i know i wish!!! we actually were in talks with a publisher about doing a coffee table book back when i put together 150 photos of vintage lesbians, but the process with securing print reprint rights for all the photos turned out to be more trouble than the book would’ve ultimately been worth. hopefully when I move to LA i’ll have more access to and knowledge about that process because the biggest LGBT archive is at the USC library and can talk to real humans about where the pics come from and what one would have to do to republish them.

      • ahem. hi from this queer archivist friend just down in San Diego! eagerly and very sincerely volunteering my archivist skills and knowledge and southern california queer archives connections for projects like this when you get here. seriously, lmk if you want some intros or some tips – i’d love to help!

        (ps: assume you already know this, but in addition to the folks at the ONE archive at USC, the june mazer collection has some INCREDIBLE pieces of queer women’s history.)

  7. Not to be too critical cus this is awesome herstory, but can we maybe not frame this as ‘omg hot butches’? Feels a bit like this isn’t targeted at butch women at all but just people who think they’re hot.

    • yeah, esp bc autostraddle (esp the comments) has such a history of framing butches as gross and basically men. like, sooo… you don’t want us around as people, but you do think we’re totally smokin? ok

    • Ok it took me 4 days to be able to read the replies to this comment but I have! And thanks for not hating me! I know it sounds stupid but I really worry what people on Autostraddle will say. On the negative side that makes me a shallow person who relies on feedback from the internet to make me feel ok, on the positive side at least my frame of reference is a bunch of cute queers.

  8. What a great article! Thanks for the hard work. These women must have had such interesting lives, not without heartache, I’m sure, none of us escape that but what an exciting time to be young.

  9. Thank you for this! I looked up Tiny Davis and I just have to share my favorite line from her Wikipedia page: “Among her sidewomen was bassist Ruby Lucas, who became Davis’s lover; they opened a club, Tiny and Ruby’s Gay Spot, in Chicago, near the end of the decade.”

  10. Thank you so much for featuring Annemarie Schwarzenbach! I’ve also been obsessed with her since I first stumbled over some of her pictures and writings. She was such a fascinating person and a great writer as well! Also, tremendously gay.

    And there are so many awesome people on this list that I need to research now… 🙂

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