Holly came from Miami, FLA
Hitchhiked her way across the USA.
Plucked her eyebrows on the way
Shaved her legs and then he was a she
She says, Hey, babe, take a walk on the wild side
I remember the first time I saw my father dressed in women’s clothes. Well, to be fair, it was also the last time, and technically only half of him was in drag: he’d cobbled together one of those half-men/half-lady getups for a neighbourhood Halloween party. But it was still an edifying experience, watching the man who would frequently cuff my ear for looking too “girly” sweating profusely as he stuffed himself into my mother’s tatty, stained white bustier.
It wasn’t until my early 20s that I discovered a whole industry devoted to helping fellas fit into shapely corsets and heels that don’t pinch. My friend David Bateman was working at a place called Take a Walk on the Wildside, Toronto’s first store devoted entirely to transsexual men, crossdressers and drag queens, and offered an after-hours tour of the shop.
Michelle DuBarry and Aldridge in 1977.
It was an epiphany. Walls were lined with a glorious rainbow of stiletto heels, while clothing racks sagged with enough PVC, feathered and lacy garments to fit even the most zaftig of wannabe princesses. Two dizzying hours later I had tried on everything in my size, danced around in boots, platforms and kitten shoes, and plonked more wigs on my head than Bert Convy. Thoroughly exhausted (those spandex cat suits are a killer to pry off), I was then carted upstairs to meet the owner of the shop, a woman named Paddy Aldridge.
I think it’s safe to say that you have never met a woman quite like Paddy. Statuesque doesn’t come close to describing her majestic height of six feet or the robust curves that must make many of her crossdressing clientele green with envy. When I first met this amazon, she sported a shock of red curls, perfectly suited to the joyful, buoyant voice that put me instantly at ease. Here was a woman so welcoming and non-judgmental that any feelings of embarrassment at the discovery of my dressing-up session quickly evaporated. It’s a quality that’s clearly served Aldridge well in her line of work, given that Wildside recently celebrated its 25th anniversary in business.
“There are always first-timers who are maybe a little nervous at taking their first step into this,” Aldridge says. “I try to make them feel comfortable and safe. I’m here to help transform them into a woman, but I’m also here to listen to their story, and to what’s brought them here.”
Aldridge performed as stripper Fancy Free in the 1970s.
As deliciously complex as those stories must be, most would surely pale in comparison to Aldridge’s own personal history. Wildside might seem a daring and eclectic enterprise, but it may well be the most conventional element in a life filled with excitement, drama and embracing the unexpected.
The adventure started when Aldridge was 18, having just moved out of her parents’ Leaside home to take up residence with her best friend and his two roommates. “My mother was horrified,” she laughs. “But I told her, ‘Mom it’s okay; Robbie’s gay!’”
One can only wonder if such a revelation set the elder Aldridge at ease. Despite a conservative upbringing — complete with convent training — little Paddy was clearly turning into quite the wild child and threw herself into the heady nightlife with rapturous abandon.
Sadly, woman cannot live by beer and disco alone. “My friends sat me down and said, ‘You need a job,’” Aldridge remembers. “So I went to stripper school.”
The year was 1973, and the school in question was situated above Le Strip, a Toronto institution renowned for its naked girls and raucous audiences. The stripping industry was different back then, emphasizing glitzy costumes and showmanship over a mere pussy parade; panties were still part of the uniform, not something to be slung at the nearest frat boy waving a $20 bill. Armed with training, a stripping agent and a brand new nom de guerre, Aldridge was now Fancy Free in both name and nature.
She remembers the stripping years fondly: a whirligig of sequins, feathers, free drinks and camaraderie. But there was also a dark side to the fabulous life. “These nightclubs had lots of drugs,” she says. “Everybody was on bennies [speed] because nobody wanted to gain weight.”
Aldridge poses with Sky Gilbert at Toronto Pride.
Looking at photos of Aldridge from that period, it’s easy to see why she was such a hit. Her impossibly long legs, tiny waist and magnificent cleavage must have been a welcome change from the skinny hippy look of the 1970s. Even now, her arresting height and fine figure place her visually younger than her 57 years. She puts it down to good genes — and mud wrestling.
“My stripping agent would send me down to Winnipeg to be a mud wrestler,” she says. “We wrestled in potter’s clay mixed with pieces of foam. It was so much fun, and it gave me really great skin.”
Things were becoming a little less fun back in Toronto. Her parents were aghast to discover that their daughter was peeling for a living, and her then-boyfriend was having his own reservations. It was Christmas time, and he’d just informed Aldridge that he’d be attending his family’s festivities alone. Turned out he loved having a stripper for a girlfriend but worried mater and pater might not share their son’s enthusiasm.
A tentative suggestion that Aldridge and her beau keep her job under wraps was met with staunch opposition. “He said, ‘Are you suggesting I lie to my parents?’ And I’m thinking, ‘No, I’m suggesting that you don’t fuck a girl for six months and then tell her she’s not welcome for Christmas!’”
The relationship went kaput, but the conflict spurred Aldridge into some long-term career planning. A friend suggested that she apply to Ryerson’s theatre school, and she began her studies in the technical field that autumn. A student loan of $4,000 helped pay the bills, while she moonlighted as a sex-trade worker. Three years later she graduated debt-free, with a house, paying tenants and a perfectly respectable skill set to which no boy’s parents could reasonably object.
It was now 1986, and Aldridge was building floats and creating costumes for the Santa Claus Parade. A friend who knew of Aldridge’s skill with makeup and sewing suggested that she start offering her services to drag queens and crossdressers. One ad in Now magazine was all it took: “Take a walk on the Wildside. Who’s that girl? It could be you.”
“The phone started ringing off the hook,” Aldridge says. “I would start transforming people at 10 in the morning, right up until nine at night, six days a week.”
A lot of Toronto’s premier drag and trans personalities have made their way through Wildside over the years: Enza Anderson
, Sky Gilbert and a host of karaoke queens found their first pairs of heels behind those safe and welcoming doors.
“When it comes to crossdressing, female impersonation or just trying to find the femme inside you, Paddy is the ultimate drag mother,” Anderson says. “She started something that very few have dared venture in and has come out supporting a community by creating a social gathering, as well as a place to pick up big, fabulous hair.”
Bateman shares Anderson’s gratitude for the safe space Aldridge has created in Wildside, as well as the opportunity to make a living while sporting falsies and a wig. “I have to say, it was a truly wild, whacky and wonderful experience working at Wildside over the years,” he says. “I was given a lot of memorable opportunities that a fledgling crossdresser might never have had without Paddy’s brash and fabulous bravado and her big, wild heart.”
Aldridge’s passion for Wildside meant long hours on her feet but also the chance to attend workshops and conventions for crossdressers. It was while attending a seminar in Boston that she met the person she would marry, a trans woman named Veronica Brown. The couple became quite the cause célèbre, with numerous magazine and television appearances, including a bittersweet segment on The Phil Donahue Show, where Veronica’s biological daughter was one of the program’s callers.
“She said, ‘Veronica is my father,’” Aldridge remembers sadly. “Phil asked if she wanted to say hello to Veronica, and she said no, she wanted to remember him as he was and that it was very painful to see him this way.”
Aldridge with Phil Donahue in 1993.
The marriage was short-lived, with Aldridge and Brown divorcing shortly after they moved Wildside to its current Gerard Street location. Here again the business would be the catalyst for Aldridge’s next serious relationship.
Thomas James Sloan was a good-looking, self-assured man who liked to crossdress. Paddy was instantly smitten and welcomed her new lover into her life and livelihood. As Roxy, a blonde bombshell in heels, Sloan proved a hit with customers and media alike; he made appearances on Mike Bullard’s show and Breakfast Television. He was glamorous, articulate and witty, but working side-by-side with a romantic partner proved a mixed blessing. Both were alcoholics, and Roxy’s newfound fame went to his head like cheap champagne.
“If crossdressing was the drug, then Roxy overdosed,” Aldridge says. “Not only was he fulfilling his dream of crossdressing, he was also a star. So he didn’t want to do any of the work.”
They divorced after five years of marriage, with Aldridge resolving to create a life outside of Wildside. She took up skiing and skydiving and spent more time away from the shop. But weariness had set in, and Wildside’s 15th anniversary found its owner taking stock of her life. “We were having a big party for the anniversary,” she remembers. “It was wonderful, but all I could think was ‘Oh my god, I’m exhausted.’”
Eight days later she was on a plane headed for the Edgewood rehab centre in Nanaimo, BC. She stayed for a year. “Suddenly, I was with people like myself. People in recovery. I had to learn to sit down and not do anything . . . to just be.”
It was her father’s death that brought her back to Toronto, to the business that had given her so much and taken so much in return. “When I came back and saw the life that I had come from, I knew very well why I was drinking. Until then, I hadn’t done anything besides work with transgender people. Customers would break down and cry because, for some, it was the first time they’d told anybody that they crossdressed. I was like their therapist, and nobody prepared me for that.”
A client in a French maid costume cleans Aldridge's office.
She also began to examine her complicated relationship with the father with whom she had never felt close. “My brother and I were adopted, and there was always something missing. Dad explained to me before he died that, two years after they got us, he didn’t want us anymore.”
She seems sad but accepting of her father’s revelation. “That’s the thing about sobriety,” she says. “You have to know your truth and be honest.”
The relationship with her mother was much healthier, and the two remained close until her mother’s death last year at the age of 92. That’s not to say there wasn’t some lingering friction. “Even when I was 35 and would go home for dinner, she’d come over and say, ‘Are you still a stripper?’” Aldridge laughs. “Mom, I’m nearly 40!”
Returning to the day-to-day operations of Wildside was challenging, but Aldridge felt strong in her sobriety and in a new relationship with a woman named MJ, whom she met during her year in Nanaimo. I make the mistake of asking if this was her first relationship with a girl, and she quickly puts me straight.
“What’s a girl?” she asks. “Would it be somebody who was born a man and became a girl? Would it be a man who liked being a man but thought he was a girl? Look, I’ve been to bed with lots of combinations and I never turned anybody upside to see what they are. I fall in love with the mind.”
The relationship didn’t last long, but it showed that Aldridge could get through a breakup without booze — something that had proven difficult for ex-husband Roxy, who drank his way through a generous divorce settlement and was now living, finally sober, in a homeless shelter.
The two reunited, this time as friends, with Roxy lending support during Aldridge’s 2009 battle with uterine cancer and subsequent hysterectomy. Sadly, as Aldridge’s health improved, Roxy’s began to decline. He was diagnosed with liver and pancreatic cancer and died in 2011 with his ex-wife holding his hand.
These days Aldridge has created a more balanced life for herself. She started painting during her recovery, and many of her efforts hang in the gallery that she’s installed on Wildside’s second floor. This is her 10th year of sobriety, and life has settled into a rhythm that suits her nicely.
“There’s always something to do every day,” she says. “In sobriety you see a different reality than the one that you’re used to when you were drinking. And the new reality is just a beautiful life.”
Wildside is located at 161 Gerrard St E. See wildside.org
for more details.