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Rori Scheffler

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The Right Fit

How one Midwestern boutique is evolving with the trans community

It’s a Monday in June, and Olivia Connors is perched inside the picture window of Transformations by Rori, draping mannequins in red and black, Chicago Blackhawks colors. Connors, a trans woman in her 60s and a former president of the Chicago Gender Society, works part-time as a sales associate at Transformations, a boutique in the Chicago suburbs with a diverse customer base that includes trans women and cis male cross dressers. The Hawks are vying for the Stanley Cup; a little sartorial support can’t hurt.


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Inside Transformations, poster-sized pinups of Marilyn Monroe hang near a leopard print stiletto-shaped chair. Wigs cascade from styrofoam heads; hand-sewn sequined cover-ups and dresses in lime green, royal purple and other vibrant colors fill the racks. In a boutique that celebrates old school glamour and elegance, a window display honoring a sport notorious for its violent on-ice scuffles might seem at odds. But Connors doesn’t see these worlds as contradictory.

"I don’t wake up looking like this," says Connors, who at the moment wears a scoop neck dress and full makeup. "I live my life the way I want to. Sure I get looks, but you smile back. And people go, ‘Oh, okay.’ I think a lot of it is confidence. And if you have that confidence in yourself, you’ll project that to other people."

From left: Scheffler, a friend, Connors. Image: Transformations by Rori

Helping others feel confident and comfortable in their own skin is part of what Connors and Rori Scheffler, a cis woman in her 60s and the owner and founder of Transformations, do for a living. The 25-year-old boutique is tucked away in unassuming brick building adjacent to a Starbucks and an Ann Taylor Loft in Arlington Heights, a suburb about 40 minutes outside Chicago. Only the bright red Transformations sign outside vibes with the boutique’s high femme aesthetic.

Discreet but accessible, Transformations has long provided a safe space for the transgender and cross-dressing communities in Chicago and throughout the Midwest. The boutique opened in 1990, the same year a trans woman made headlines after she was kicked out of the Michigan Womyn’s Music Festival because she broke its "woman-born woman" policy. 1990 was also the year the Americans With Disabilities Act lumped transgender individuals together with pedophiles for behavior deemed "immoral." At a time when — despite the work of trans activists — institutionalized discrimination against trans people was accepted by the mainstream, opening a boutique that allowed individuals from across the gender spectrum to shop without fear of judgement was nothing short of radical.

The boutique opened in 1990, the same year a trans woman made headlines after she was kicked out of the Michigan Womyn’s Music Festival.

But a lot has changed since Transformations first opened its doors. We now live in a world where activist and author Janet Mock's wedding receives elated coverage, where Amazon’s hit show Transparent won two Golden Globes, and where the constitutionality of the ADA’s shameful discriminatory stance is finally being challenged.

But despite greater visibility and more nuanced, authentic representations, our world remains one where trans people, particularly trans women of color, are disproportionately the victims of violence. Even as trans issues inch closer to the center of the cultural conversation, the voices of trans women, men, and genderqueer individuals are still marginalized. So what does this contradiction mean for safe havens like Transformations that began on the margins?


Some Transformations customers identify as women, some don’t. Some are cis women who’ve had mastectomies, and are contending with how losing their breasts impacts their sense of self. (Transformations also sells breast forms and mastectomy products; cancer patients are also regular customers.) But for one reason or another, they are there, says Scheffler, because they want to make "what they feel on the inside match what they see on the outside."

Says Scheffler, "We try to help them feel not self-conscious, and ease into that feminine side."

But that can be tricky. While there’s no singular form of female expression, trans women often face pressure to conform to societal standards of femininity.

They want to make "what they feel on the inside match what they see on the outside."

"The prettier you are, the easier it is. You don’t get ridiculed as much," says Connors.

Amplifying stereotypically female cues through clothing that, for example, accentuates the waist and hips and deemphasizes larger hands and broader shoulders, is often about more than mainstream acceptance. As of October, 21 transgender people have been murdered in the United States in 2015, the majority of them women at the hands of romantic partners. Being able to "pass" as female can also be a vital matter of safety.

On the flipside, focusing too much on feminine beauty can be problematic. The persistent, damaging conflation between cross-dressers, drag queens, and trans women undermines the latter’s gender identity, which is neither a choice nor a performance.

Some Transformations customers prefer a full Scheffler makeover: Beard cover, multiple layers of foundation, brow camouflage, and shading to lift the cheekbones, soften the jaw and maximize the space between eyelashes and brows — plus buying a dress, wig and heels. Others prefer a less traditionally high femme presentation. Still others take a DIY approach: Scheffler recalled one customer who melted down rubber fishing worms and molded prosthetic breasts from them. Another, a carpenter, rigged a wire into a body shaper to create impressive cleavage.


"I have loved everything I did in my life, and I’ve had more than one dream come true. I’ve always wanted to be a performer, and I loved makeup," says Scheffler, who wears wigs, striking eyeshadow, false lashes, and statement jewelry.

Her dreams came together in 1989, when she owned a nightclub/restaurant in downtown Chicago half a block from the Baton Club. The Baton Club is a performance venue known for its campy, Las Vegas-style revues starring celebrity impersonators and drag queens. Former performers include Candis Cayne and Alexandra Billings, who stars in Transparent and made history as the first openly transgender female actor to play a transgender character on television in 2005’s Romy and Michele: In the Beginning.

Wigs at Transformations. Image: Transformations by Rori

Today, about 60% of Baton Club performers are transgender women and 40% are gay men, says owner and founder Jim Flint, who has seen tectonic shifts in the club scene since it opened in 1969.

"Back when I started it was a hidden thing, it wasn’t exposed it at all. We didn't open it up at all," says Flint.

Scheffler frequented the Baton Club, and her son, Soto Petropoulos, who identifies as gay and a cross-dresser, worked there for many years. Her experience later led her to return after opening Transformations.

"Rori used to bring large groups of transgender people in, and bringing them in, she did a great service by exposing them to us," says Flint.

Around that time, Scheffler was also hosting ladies' pampering parties at her own club. Different jewelers would come in, and once in awhile Scheffler would do a makeover. One day, Scheffler was approached by the president of the Society for the Second Self, a support group for cis male cross-dressers, their partners and families, who was looking for a place to host the organization’s Christmas party. Scheffler’s club/restaurant came to mind.

"I gradually built the business, and kind of grew with my business."

But before the holidays arrived, her club folded. Scheffler knew it was time to switch gears. The following year she opened Transformations at its first location in Oak Park, IL, applying her experience in costuming and makeup to retail.

Says Scheffler, "I started with earrings, wearable art, and expanded into wigs. The makeup line took about a year to develop, breasts forms came last. I gradually built the business, and kind of grew with my business."

About a year later, she ran into the president of the Society for the Second Self. When Sheffler told her about the new business, she asked if Sheffler would be willing to do a presentation for her group. Of course, Scheffler said yes. Attended by both cross-dressers and trans women, the meeting was Scheffler’s first introduction to what she calls "the gender community." It was also a learning experience.

"I was amazed," says Scheffler. "It was the third Saturday in March, we had the worst snowstorm of the season, and there were 71 people in this little room, and about five from out of state."

Connors at Transformations. Image: Transformations by Rori

Over the years, Transformations grew into a hub of community and a regional destination. Scheffler even hosts an annual Halloween Extravaganza and Glitz 'N Glam parties where customers can "dress out." Many longtime customers, like Karen, a cis woman, and her wife Nicole, a trans woman who began transitioning in the 1980s, consider it more than just a retail business. The couple first learned of Transformations in the late 1990s when it was featured on the PBS show Wild Chicago.

"Rori has a huge support system for the trans community. She welcomes all into her store and makes everyone feel at home," says Karen.

Scheffler has succeeded by understanding the needs of her customer base. She prides herself on promoting events that build community, selling clothing that’s "washable, wearable and affordable," along with speciality garments that are unavailable in department stores.

Scheffler hasn’t raised most prices in 25 years. Though Scheffler says her prices are reasonable, some customers feel guilt and shame over the "indulgence" of buying a second wardrobe.

"People come in, they want a sale wig, and then they’ll go shopping at Goodwill or Salvation Army. I mean, they’ll buy their bras there. I say, decide where you want to start," says Scheffler. "I don’t ask anyone’s preference. But sometimes you have someone sitting in the chair that just tears up because they feel so good about the experience. It’s the most rewarding thing in the world to help somebody take that step."


Trans issues entering the cultural conversation has meant that a binary view of gender — hard and fast categories of male and female — is now being recognized by the mainstream as limiting and inaccurate. Facebook users can now select from 58 different identities, including gender fluid, trans female, trans male, and two-spirit. Models who identify as gender neutral regularly strut down high-end runways. Recast within this new framework, some things about Transformations might seem a little anachronistic, or dated.

"We can no longer assume that one transgender person has the same style as another."

For instance, using terms like "masculine" and "feminine" is something that Daniel Friedman, 36, the founder of Bindle & Keep, a bespoke men and womenswear company that counts Laverne Cox among its clients, steers clear of. The store is "gender blind, but not gender stupid" says Friedman, who knows that many customers have had painful experiences, and that as a result, certain words can be triggering. This ethos guides their custom suit design process.

"We can no longer assume that one transgender person has the same style as another transgender person," says Friedman. "Clothing is not vanity, in this case. It's about feeling correct. We don't look at it [a suit] and say, 'Are you feeling your gender?' We say that it finally matches your aesthetic." Continues Friedman, "We don't talk in terms of masculine and feminine. We feel that's dated, and everyone has their own definition of what those terms mean. They can mislead our clients. We talk very much in terms of fit."

Both Friedman and Connors say that the right apparel can help an individual align their external appearance with their inner sense of self. But they’re also both conscious of how a style shift can come with unrealistic expectations.

"When people put on a suit for the first time, it's not this panacea. It’s not this magic suit," says Friedman. "I always feel like it's most important that [customers] are at least satisfied with who they are before they go forward into the transition," says Friedman.

"They customize themselves. They are customized people."

Though one of Scheffler’s goals is to make customers as "beautiful and passable as they can be," it’s never to make carbon copies. Both Scheffler and Friedman ask people to find a magazine image or a celebrity style crush that reflects their desired aesthetic. In part, finding the right fit is understanding exactly where customers want to go. And part of that is understanding where they came from.

Says Friedman, "They customize themselves. They are customized people. They need to feel like they are heard."

Connors, too, often starts working with customers by simply asking what they want. And, she says, when they find something that resonates, it’s obvious.

Says Connors, "I can tell instantly, and I know what they’re thinking, and they know what I’m thinking, and it clicks when it’s right."

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