pic2016. CBC photo.

Harold Anderson

1938 - June 23, 20241

In the 1980s and '90s, Anderson became a fashion fixture on the streets of Halifax and in the reading room of the city library.

In 2016 the then-78-year-old described his choice to CBC's Information Morning. "Bright red pumps, four-inch heels, four-inch stilettos. Patent leather red."

Anderson, who was straight, unmarried and with no children, didn't wear his heels out in public until 1982, "right after Pierre Trudeau brought in the constitution."

He wasn't entirely comfortable with the term cross-dresser: "It is essentially correct, but I don't like putting any kind of labels on people," he said. "And you don't hear women being referred to as cross-dressers just because they wear pants."

I don't feel that as human beings, we should have to have our likes and our dislikes governed by our gender.2


The Reluctant Gender Pioneer

By Lisa Cochrane

Halifax has lost one of its most enigmatic yet beloved characters, a person about whom nearly everyone of a certain age has an anecdote but someone very few people know anything about. Harold Borden Anderson, a long time Halifax resident, the modest man wearing the blazing high heels, has died peacefully aged 86.

Many will recognize and remember “that shoe guy,” Halifax’s eccentric cross-dressing pioneer who began strolling along the Spring Garden Road area in the 80s in all manner of lady’s wear, most notably in his beloved stiletto heels. Harold owned dozens of pairs of heeled shoes. All his life Harold enjoyed nothing more than being complimented on his choice of elegant footwear and on his shapely legs, or on the effortless manner with which he was able to walk in his three to four inch heels. For Harold it was an important aspect of his identity, his pride and joy I remember early sightings of Harold in his grey business suit with bright yellow or red pumps popping out from underneath his trouser legs. It was intriguing to witness this brave mystery man break with social convention decades before gender fluidity became the accepted norm it is today. Eventually Harold grew in confidence and graduated to wearing pencil skirts and World War II era seamed nylons with geometric heel patterns. Harold looked like an average man from the waist up - no frilly blouses nor makeup for him - and an elegant woman from a by gone era from the waist down. Harold intrigued me, as he did his many admirers over the years.

I got to know Harold in the early 2000s while developing a documentary film about him. It quickly became apparent however, that Harold worried the media scrutiny might get him fired from his job as a night security guard, so I let the project drop. It was hard to forget Harold’s good humour, hunger for companionship and the colourful stories he’d shared with me about his life. Over a decade later I wrote a play about a documentary filmmaker and her reluctant subject called Well Heeled. The theatre production precipitated a reunion with Harold from which a friendship developed which lasted until the end of his days.

Harold grew up in Middle La Have on the South Shore of Nova Scotia, the eldest of two sons born to a fisherman and his wife. Harold was drawn to lady’s footwear from a very young age. “I’d get a thrill seeing a dainty shoe dangling from the end of a feminine foot,” he’d say, while questioning why social convention forced him to walk about in self-described clodhoppers. Harold was caught once or twice wearing his mother’s heels, and was admonished with the likes of, “You’ll never get a job or a wife up in Halifax wearing those girly shoes, Harold.” Harold did get a job in the city, several jobs over the years, but always while wearing conventional male clothing.

Public Harold and private Harold were at odds throughout his life until middle age however, when Pierre Elliot Trudeau declared that the state had no business in the bedrooms of the nation. Thus emboldened, Harold ventured into a police station to question whether it was illegal for a man to wear feminine attire in Halifax. Once he determined it wasn’t, Harold began to step out in public – first only at night then gradually in daylight - in whatever mode of dress made him feel happiest inside.

Harold wasn’t entirely comfortable with the term cross dresser, because he didn’t believe in putting labels on people. “My likes and dislikes should not be governed by my gender,” Harold mused. “Women weren’t called cross dressers for wearing pants, so why is there a double standard for men?”

Lifelong bachelorhood was Harold’s fate, but he lived in eternal optimism of finding the woman of his dreams; he once confessed that he’d been looking for a wife since Expo ’67. Although many people might have assumed Harold was gay, they were incorrect. In his view, he was a normal man who simply exercised the right to dress how he pleased. Romantic love eluded Harold, so he contended himself with the many casual encounters he enjoyed with strangers over the years, and of course he had his hobbies.

Harold held a series of modest jobs during his working life – bank teller, debt collector, bookkeeper for a men’s clothing store – but his ardent dream was to become a country music radio DJ. Harold was passionate about – and had an encyclopedic knowledge of – ‘old style’ country music from the 40s, 50s, and 60s. Over the years he amassed an extraordinary collection of rare 78s, 45s and LPs from many admired country artists, like Wilf Carter, Hank Snow and countless others. Harold could curate a song for any occasion, knew all the lyrics to his favourite music, had memorized the career trajectories of each artist, the details of record label mergers; all of it fascinated him.

When his radio career failed to materialize, Harold began a long-term project, multiple recordings of a fictitious country music radio show he called the La Have Country Jamboree. ‘On air’ from his small private quarters, Harold’s alter ego, the witty radio announcer Mr. Calby Parker, cracked puns into the microphone between spinning records from his private collection. ‘Calby’ worked with a host of other named station employees, each with distinct voices, personalities and relationships, all performed by Harold according to his carefully prepared scripts for each recording.

Eventually, via a mail-in country music fan club, Harold connected with an ethnomusicologist from Glasgow, Scotland who acquired many of Harold’s fictitious radio tapes, which numbered in the dozens, over many years without the two men ever meeting.

Harold’s other passion was classic American cars. The big ones. He had a pristine collection of Classic Car magazines that no one else could touch, a floor-to-ceiling display case of prized miniatures of his favourite automobiles, and a steel trap memory for car details. He even wrote a novel set in an American car factory. If we’d see a classic car on the road, Harold could immediately identify the make, model, year and point out its distinguishing features.

“If you’re going to drive, why not drive in style?” was Harold’s motto. Until he became wheelchair-bound due to arthritis in the last few years, Harold drove a Burgandy 1976 Buick Electra, or “our car” as he called it, for I did most of the driving. Before the Buick, Harold drove two Pontiac Parisiennes into the ground without knowing how to pump his own gas, one of his many foibles. Despite his dependence on gas jockeys, as he called them, Harold loved nothing more than taking long country drives throughout Atlantic Canada and New England, and he especially loved hilly terrain and winding roads with rural vistas.

To say Harold had a phenomenal memory would be an understatement. He knew baseball statistics, multiple quotes from his favourite television characters, and remembered the exact date we met and how our friendship began. Harold had a childlike, naïve quality about him at times; in other moments he could be stubborn and fiercely independent. Puns and word play expressed Harold’s mischievous nature and keen intelligence. He also enjoyed bombing me with random anecdotes from his life back in the 60s, usually when I was behind the wheel of the massive Buick in highly stressful driving conditions requiring my complete concentration.

Harold was kind, witty and eternally optimistic, happy to go anywhere I was willing to take him. I enjoyed his company and our shared adventures immensely. I now have much material from which to shape a video portrait of the man in the heels, in the works.

Harold is survived by his younger brother Borden Anderson and sister-in-law Beverley Anderson of Ontario, and their extended families.


Bob O'Neill: "A courageous and self-authentic man. He should be recognized for his contribution to fostering gender fluidity."

Gary Hanrahan: "Harold worked for a while in the Finance section at Public Works while we were still in Maritime Centre, so I got to know him "in person", not just from seeing him around downtown.'

Gary Marsh: "When I first moved from NL to Halifax in '03, friends of mine who had been in Halifax before told me, "keep an eye open for skirtman!" "what?"... then one day I'm on Spring Garden, I glance across the street and there's a random dude over there wearing a business-y outfit, but with a skirt and bright red heels - it was the legendary skirtman I was told about, in the flesh! And I was just as struck by how indifferent everyone else around him was, like it was just a normal day in downtown Halifax. I felt right there that I moved to the right city."3

Shiju Matthew: "Activism doesn't always have to be loud chanting and parades. It can simply be a pin stripe suit and red stilettos. My very first day in Halifax , in 1999, on Spring Garden Rd, I heard a clicking sound of stilettos and looked back to see a man in pin stripe, 2 piece suit walking elegantly in red pumps. In that moment I knew, I could be me in this new life and place." 4

TumaYoung: "I used to see this man walking around Spring Garden road and knew that he was part of Halifax and Halifax was part of him. A straight man who at the vanguard of gender fluidity. We would all ask ourselves who was this gentleman wearing red patent pumps? There were many theories- a civil servant, a millionaire, an eccentric, but we all agree that he was part of Halifax’s soul and character."5


November 4, 2016 Harold Anderson's choice of shoes inspires Halifax play. In-depth CBC interview including notice of the play, Well Heeled.

2018: Harold Anderson - 80 year old, country & western, cross dressing DJ A feature on Harold in Applied Arts Magazine

June 26, 2024: CTV News: Halifax Icon Who Wore High Heels With Pride Dies at 86

Celebration of Life

A celebration of life for Harold will be held on Friday, July 12, 2024 from 4-7pm at The Local, 2037 Gottingen St. Halifax.

Anyone interested in celebrating Harold’s life and enormous impact is welcome to join his friends and family at The Local bar on Gottingen Street.

People will have an opportunity to publicly share what Harold has meant to them. Joining in the celebration implies consent to be filmed for all media projects being developed about Harold Anderson’s life and tremendous social impact.

No RSVP necessary. For more information, email ljcstory@gmail.com.


1. tweet by @JackieTorrens
2. The November 4, 2016 CBC interview
3. June 25, 2024 Comment on the WayvesMagazine post
4. June 27, 2024, his Facebook feed
5. June 24, 2024 his Facebook feed