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HALIFAX - Harold Anderson, a Halifax man known and admired for the elegant stilettos he wore on his jaunts around the city, has died at the age of 86. His longtime friend Lisa Cochrane says the fashion-lover who challenged gender norms will be remembered for his brave self-expression and style. “He really didn’t like the term cross-dresser.

He didn’t like the labels that were put on people. He’d say: ‘women wear pants all the time, why aren’t they called cross-dressers?’” “He just didn’t have time for any of that. He didn’t think his fashion choices should be defined by his gender.



He really was a sort of trailblazer,” Cochrane said in an interview. Cochrane, an artist and filmmaker, first noticed Anderson walking around Halifax in the 1980s, wearing a suit and four-inch heels — either yellow or red. She felt drawn to the man who seemed so happy, and in the early 2000s she introduced herself.

Shortly after, she started working on a documentary film about Anderson, which she dropped when she realized Anderson had become nervous about how such a documentary might impact his work as a security guard. Then, more than 10 years later, she wrote a play about a filmmaker and a reluctant documentary subject who wears elegant high heels and reached out to Anderson to see what he thought. This time around, he was happy with the idea, and the play called “Well Heeled” was commissioned by the Halifax-based LunaSea Theatre Company.

It ran as a workshop product.

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