Harold Anderson knows his shoes.

"Bright red pumps, four-inch heels, four-inch stilettos," the 78-year-old says, as he describes his choice to CBC's Information Morning. "And this is patent leather red."

After first screwing up the courage three decades ago to sneak out at night in his heels, Anderson has since become a fashion fixture in the streets of downtown Halifax.

But he isn'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 says. "And you don't hear women being referred to as cross-dressers just because they wear pants."

His fashion choices have attracted attention for several decades, and had long caught the eye of local artist Lisa Cochrane. She has now written a play inspired by his story called Well Heeled.

Artist Lisa Cochrane grew up seeing Harold Anderson around Halifax in his heels. (Phlis McGregor/CBC)

'A stupid, social, sexist convention'

Anderson first paid close attention to women's footwear while he was still in school and he noticed what his female classmates were wearing.

"They would wear these little patent leather pumps and sometimes dangling them on their feet," he says. "That used to get me."

He says he liked the style and design of high heels. That was in contrast to the "god-ugly clodhoppers that we men are supposed to wear, simply because we are men," what he calls "a stupid, social, sexist convention."

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

He would go out under the cover of darkness at first, but that's not what he wanted. He eventually got the courage to go out in daytime. He wanted freedom.

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

For awhile, a lot of obscene remarks came his way. That doesn't happen much anymore.

'Take the plunge'

Cochrane grew up spotting Anderson around Halifax "mostly in pants and high heels." It occurred to her that he seemed so happy.

"It seemed to me that you were exploring and more accepting of your femininity than I have been in my life," she says. "It's something I always denied in a way."

Harold Anderson (Phlis McGregor/CBC)

Anderson does have advice for those wanting to try something different: "take the plunge" and don't ask other people.

"You're only going to get negative answers and they're gonna try to stop you," he says.

LunaSea Theatre will present a staged reading of the play Well Heeled tonight and Saturday at the Waiting Room on Almon Street in Halifax.