I tried hard to pass in medical school, Medical College of Virginia, from 1989 to 1993.
Not pass as straight. Pass as "normal", whatever the hell that means. I was newly married but my husband was planning to be a house husband while our kids were little. Actually he planned never to work again, but he was lying to me when he said he'd go back to work. Anyhow, he was a golf and tennis pro and was lazy faire and also tended to dress in drag. Actually not drag. Genderfuck was how I thought of it: he was clearly male wearing women's clothes and enjoying the reaction.
He lay low while I was in medical school. At least, he lay low in Richmond. When we went back to the DC area to go dancing, he'd dress up. I didn't care. I was studying hard.
Once in the elevator, one of the other female medical students was talking about her husband. "I threw out all of his plaid shirts. When he wasn't looking. I hate plaid shirts, low class." I wanted to respond, "Oh, yes, I hate when my husband wears my plaid skirts, he stretches them out. I tell him to buy his own." I did not say it. I stood there poker faced while I thought it.
I tried to pass but was not terribly good at it. I was raised by time warp atheist but sing masses in giant choruses beatniks, who liked to have folk song parties. No television until I was nine, so I didn't care much about television. Boring. Hiker, biker, skier, dancer, swimmer. I'd missed out on ball sports. I did play volleyball in medical school and it was loads of fun.
One time my sister was visiting and we ran into two southern belle MD students in a mall. One said she couldn't find the right shoes for a wedding. "Ah could only find white with navy trim, not navy with white trim." "uh, what's wrong with that?" "You cain't wear white shoes after Labor Day!" "Oh, uh, yeah, right." As I think, gosh, my beatnik mother really didn't give a shit about the rules and didn't teach them to me......My sister agreed. That rule had escaped her too.
When my sister was in junior high, she had a cohort of female friends. My mother called them the clones. They dressed alike and my sister too. My sister got saddle shoes in 6th grade and polished them religiously. My mother, in high school in the 1950s, was scornful for a bit. She wouldn't have been caught dead in saddle shoes. Then my mother remembered how much she had wanted cowboy boots and how my grandmother had refused because the pointed toes were "bad for her feet". Well, yes, if they are too small. My mother quit scorning the saddle shoes.
My sister was much better at passing than I was. It was partly because I am so busy reading the non verbal cues that people give, that I discard gender and the clothes people wear as unimportant. Well, or as only important in what the person is trying to project while the non verbal cues say what is REALLY happening. So I made people nervous. In part because in being oblivious to clothing, I wore what I liked, which was universally regarded as weird. My artist mother would wear paint stained t shirts or DRESS UP, for art openings or parties, in a hand made 1960s white pant suit, sheer layer made from Indian sari material with gold embroidery a foot wide at the hem of the bell bottoms and the hem of the fitted zip up the back tank top. I have the outfit. I am not making it up. So, I got a clothes allowance in junior high, bought what I liked, and then wondered why it was so very clearly just wrong at my school. Then I went home with a new friend. The living room had a couch, tv trays, and a television. There was one set of shelves with some plants and no books. There was a magazine. Her room had twin beds with matching coverlets, a dresser, stuffed toys on the bed and no books. I thought, holy crap, I am never ever inviting anyone from my school to my house. My house usually had some other student adult living with us, renting or free, ongoing art projects in the kitchen with melted crayons and paraffin painting flowers on tshirts, my sister and I had elaborate china doll houses on the glassed in porch where we had hand sewn the clothes, the quilts and made some of the doll furniture, some instrument or instruments being played or records, everything from the Band to Bach, and often inebriated adults. My father was in eternal mathematics grad school, my mother was an artist first and mom second and NOT a housewife, horrors. Add my disinterest in television and voila: I was practically antisocial in junior high and high school. I retreated into books, family skiing and hiking and in the summer swimming, and music. In school I played four instruments, because I could escape one class each week for a lesson for violin, flute, oboe and eventually jug band. And none of the teachers cared because the grades were good....
I managed to pass in medical school, at least enough to graduate. I was definatly in the weird med school student group and I also ran the Women in Medicine group my second year. I asked one of the blonde southern women why she was not in Women in Medicine. She replied, "Well, somebody might think I was a feminist." I blinked at her, wondering if she knew how women got into medicine. I told my husband and he said, "Let's make you a tshirt that says Lesbo Nympho Killer Whores in Medicine."
"I would like one," I said, "But I think I get in enough trouble without wearing something like that...."