Nailed to a post in Thompson, Connecticut, is a wooden sign that once read “SCARLETTS.” It stands atop a hill on a road that winds past abandoned mills and an American Legion post advertising Sunday breakfast. Now weather has beaten a letter off the sign, leaving “SCAR ETTS,” spelled in mailbox stickers, and the outline of an “L.” The whole town looks to be peeling.
Scarlett lives in a little white colonial nestled in a dip beside the road. In her basement, which doubles as a living room and beauty salon, she rips tape from a roll while her 70-year-old client, Sarah, tells me about the first time she tried on her mother’s stockings. She was 11; she still believed she was only a boy. “Relax,” Scarlett tells her, smoothing Sarah’s forehead and pressing Scotch tape onto her temples. “Your face is tensing up.”
Scarlett is applying her signature facelift, temporary by design, for clients whose families don’t know they cross-dress or wish they wouldn’t. Sarah—which is this client’s femme name, but not her legal one—was assigned male at birth and identifies as bigender, meaning she sometimes feels like a man and sometimes feels like a woman. Later that day, the fresh tape on her temples would unstick in time for the scrubbing, disrobing, and de-wigging that must take place before Sarah can go home to her wife.
Scarlett, a 34-year-old cisgender woman, has an oblong face and a smile that shows her gums. “I’m as close to a modern-day lady’s maid as there is!” she likes to say as a way of capturing all that her makeovers can entail—transformation makeup, femme coaching, wardrobe consultations, emotional support. Partial to rumpled button-ups and boot-cuts, Scarlett presents as unpretentious: What’s most striking about her is her total lack of artifice. With clients, she is plainspoken and earnest, and friends have accused her of “dressing in drab.” But a glance into the closet she stocks for clients proves her eye for glitz. A thrift store in miniature, the closet is crammed with silks, denims, leathers, and feathers; ballgowns and business blouses hang alongside cheetah-print miniskirts and bunny ears. A sequin-spattered dress is a client favorite, Scarlett told me on my first visit, plucking it from the rack and holding it up to the closet’s overhead bulb. “I love that sparkle.”
Snug in northeastern Connecticut—a region known as the state’s “conservative corner”—Scarlett is a stylist for trans women and cross-dressing men. She has built her business, Scarlett’s Makeovers, on the premise that trans women should be able to present their authentic gender identities, ideally at home, eventually in public, and at the very least in front of a mirror. As Scarlett and Sarah understand it, the “umbrella term” that is “trans woman” can mean many things. It can mean a person who identifies as a woman but was assigned male at birth—the conventional definition of transgender. It can mean a cross-dresser who identifies as a woman when she’s “in femme”—dressed like a woman—and as a man when he’s not. It can mean a bigender person, like Sarah, whose clothing doesn’t so much inspire her identity as express it.
Scarlett uses her professional name at work to avoid outing her spouse, who is a cross-dresser. “Sometimes, clients actually get really irritated when they find out Scarlett isn’t my real name,” she tells me. “I’m like, ‘Well, what’s your real name? OK, hypocrite!’ ” Downstairs, surrounded by portraits of beaming clients and long-necked ’50s film stars, she paints lips, shoots photos, designs outfits, refurbishes wigs, and guards the “femme footlocker”—11 black trunks she rents to clients who are too closeted to store their femme clothes at home. The font on her sporadically updated website is curly; the couch in her studio is well-worn. The only things polished there are fingernails.
Scarlett once told me, “I’m not super feminine.” Even so, she coaches clients in feminine presentation, or how to walk and talk like a “lady”—a tricky standard insofar as it enforces stereotypes, but, for many women trans and cis, a real aspiration. In fact, for some trans women, finding their femme is more than a hope: It’s a necessity. The word “passing” (as in, being perceived as a cis woman) is taboo in some trans communities because it privileges cis identity, casting trans identity as fake or deceptive. Still, passing can protect against harassment and violence. An activist client of Scarlett’s named Karleigh Merlot told me, “Passing at best can mean the difference between good experiences and bad experiences.
At worst, passing can mean life or death.”
Karleigh, an avid cyclist who is, according her Facebook bio, “proof that pom poms, cleats, mechas, gears, chains, wine and chocolate can peacefully coexist,” has a mantra: “You’ve got to be out.” To Karleigh, who recently transitioned, it’s as much a moral imperative as a personal necessity. You’ve got to be out because it’s good for you. But more existentially, you’ve got to be out to show the world you’re in the world. “Showing up at your job, in your neighborhood, in your community,” Karleigh said. “That’s why Scarlett’s so important—because she gets us to show up.”
If the trans community of northern Connecticut and southern Massachusetts were a family, you could say Scarlett married into it. Her spouse, who presents male most of the time, goes by Katie while in femme—a name whose popularity among trans women Katie noticed too late. “Katie from New York, Katie the firefighter,” Katie laments when she introduces herself to me. Beside her on the basement couch, Scarlett rolls her eyes.
Katie has a Wallace and Gromit smile and neat, expressive eyebrows. She works in male-dominated manufacturing for a boss she fears would fire her if he knew she cross-dressed. (For that reason, she asked that I use only her femme name in writing.) When she was 18, Katie joined the Army to support her budding family—her high school sweetheart had a baby on the way—and to try to kick what was, by then, an old habit: women’s clothing. She liked guns almost as much as she liked frills; she thought that if cross-dressing was kid stuff, shooting was man stuff, and Katie wanted to be a man. “Now, I’m a man all the way,” she told herself when she enlisted. (“I’m a maaan,” Scarlett drawled in a baritone from her side of the sofa.) “But it comes back,” Katie said. Now, she spends most of her time identifying and dressing as a man, cross-dressing “part-time” and changing her pronouns along with her clothes.
Before they were Scarlett and Katie, Scarlett did stage makeup for her college drama club and Katie attended air shows with her buddies. At Bryant University, Scarlett studied accounting, which she later deemed a snore. After the Army, Katie married her high school girlfriend; they had three children together before divorcing. (The separation was in large part due to their belatedly discovered “incompatibility,” Katie told me, and in small part due to her cross-dressing.) The way Scarlett and Katie tell it, when they met through a relative of Katie’s in 2006 and Katie told Scarlett about “the cross-dressing thing,” Scarlett said “Cool” and Katie thought “Wow.” They married in 2010.
Early on, Scarlett’s boldness shocked Katie. One Friday night before a trans conference, they were combing a Connecticut Kohl’s for outfits when Scarlett suggested that Katie—who was presenting male at the time—try on a dress in the public fitting room. “Try it on? In the store?” Katie asked, aghast. Clothes shopping usually entailed sketchy guesswork and invocations of her daughter at the register.
The dress fit. “Oh, this is gorgeous!” said the cashier when Katie laid it on the counter. The cashier looked at Scarlett. “Did you try it on?” A silence—and then Scarlett was pointing. At Katie. “Yes,” Katie stuttered. “It fits nicely.” The cashier, smiling, asked her, “Did you remember stockings?” In retrospect, Katie likes to say, Scarlett “was whittling away at my fears.”
Following the 2008 stock market crash, Scarlett lost her accounting job and started doing makeovers at a boutique in Auburn, Massachusetts, frequented by cross-dressers. The market for trans makeup, she discovered, was wide open. Within three years, her clientele had outgrown the store, so she left to found her own business in 2012. She converted her basement into a studio, chose a professional name, and planted a bright-red sign beside a country road in Thompson.
Scarlett’s salon may well be the only of its kind in rural Connecticut, but it’s hardly alone in the U.S. Outside Thompson, salons for trans women dot the country’s coasts in homes and high rises, part of a burgeoning profession one New York stylist has termed “feminine image consulting.” A Los Angeles stylist for trans women named Gina Ortiz told me that emails from out of state flood her inbox daily. “They all say the same thing,” she said: “ ‘I wish I had you in my town.’ ”
Compared to hubs like New York or Los Angeles, Trump-supporting Thompson—population 10,000—seems an unlikely home for such a salon. Interstate 395 is one of just a few roads in town wider than Main Street; red-brick factory buildings and an abandoned smokestack dot the downtown. “Hickish,” Scarlett said fondly. But she doesn’t see herself as an activist. “No,” she replied with surprise at the suggestion. “I’m much better on a micro-level.” Still, it’s hard to miss the broader political stakes of “micro-level” work like Scarlett’s at this particular moment when basic civil rights for trans people are under threat. To Scarlett, though, the transformations that take place in her basement are each as individual as women’s sizing.
“Most men don’t realize how difficult women’s clothing sizing is. There is no consistency,” she told me. Her method and manner reflect the guiding principle that there is no guiding principle for clothing women: “That first appointment, we’ll have a little talk. You know, about the pictures they brought with them or whatever. We’ll go through the closet, pick out five or six outfits for them to try. We’ll talk about how coloring looks against their skin. I always require people to bring their own undergarments: panties, hosiery, bra. I have breast forms. I have corsets, and I have hip padding.” She grinned proudly. “Most people kind of tend to shy away from hip padding.”
This fall, Scarlett planned open houses, group dinners, and Ghoul’s Night Out, an annual event hailed as one of the biggest trans Halloween parties in New England. As protesters gathered in Washington, middle-aged and elderly trans women gathered in Scarlett’s basement. Some came for the company, some for the lipstick—some for the chance to wander out of one closet and into another, hung with ball gowns and bras. Scarlett wrote on her pink-themed website at the start of the season: “Welcome to September! I’m still here.”
In her basement studio, Scarlett plucks a gray wig from a drawer and positions it on Sarah’s head, fiddling with the bangs until they hang straight. Soon, Sarah will leave to head home, where the expression of her gender identity is always up for negotiation, from little choices like whether to trim or shave her leg hair (she trims) to big ones like whether to tell her adult daughter (she’d like to, someday).
“This is almost therapeutic,” Sarah says from her stool. She turns a small jewelry box upside down, spilling rings, earrings, and bangles onto the coffee table. She touches each piece before picking out a necklace. “Mm-hmm,” says Scarlett. “Something a little bit shorter.” She tosses another to Sarah. “Do you want a hand? You’ve got the nails on.”
The makeover is done, but Sarah doesn’t leave her perch. She muses about a trip to Chili’s that she and Scarlett took together the previous year—a “watershed moment.” For the first time, she had felt confident in public and dressed in femme. “Knowing Scarlett was there,” Sarah says, “knowing if I did something stupid, she’d smack me.” On the road to Chili’s, though, she had worried: What would happen if she needed to use the bathroom? “Don’t worry about it,” Scarlett had told her. “We’ll go together.”