Mayor Olivia Chow’s first-day-of-work skirt was both playful and loaded with symbolism

Olivia Chow took to her bike yesterday for her first day as Toronto mayor wearing a sunshine yellow blazer and a particularly meaningful skirt. The choice of a miniskirt is a practical one for the 66-year-old cycling enthusiast, but also set a tone of ageless playfulness at the beginning of her tenure.

The skirt, decorated with an illustration of a Dundas West streetscape, is by Toronto fashion designer and textile artist Anu Raina. Chow also wore it during her 2014 mayoral race, making it not just local fashion, but sustainable. A thank-you note Chow sent Raina praising the skirt in 2014 via Facebook made the rounds again yesterday among supporters of both mayor and designer.

Raina describes her 2014 collection as her own “thank you note to the city of Toronto.” Chow ordered the skirt that year, along with one of Raina’s Skyline CN Tower dresses, coming to the studio for measurements and paying for the pieces herself.

The designer is especially glad to have the support from Chow since she feels a kinship with the new mayor. “It is such an honour to see her wear my clothes again. I feel I have a lot in common with her. She is an immigrant, I am an immigrant.” Raina notes Chow’s early career as a sculptor, and the fact that she continues to paint. “She is an artist, and so am I.”

Raina was born in the Kashmir Valley in India and lost her home to ethnic violence. She studied at the London College of Fashion in England before emigrating to Canada to study textile design at Sheridan College. She went on to show at Toronto Fashion Week, and opened her own shop in downtown Oakville in 2020, where she sells her custom and small batch designs. “Keeping production local helps support so many other people” in the supply chain, she says.

Raina says her illustrations “depict my love for this country and this city, and embrace people of every culture and every race.” The Dundas West street scene in particular depicts “the chaos and confusion of the city in a very loving way.” In the post-ceremony media scrum yesterday, Chow said she has no intention of stopping the city’s plan to rename Dundas.

The new mayor has an ebullient fashion sense. We most often see her in bright, cheerful colours — strong purples, cobalt blues — that declare this is no wallflower.

Her choice to support local artists and designers — and to rewear her favourite pieces over the years even for the most prominent days in her career — is a big part of her messaging; we’ve never seen her in designer logos. And over the years that she’s served the city in both municipal and federal ridings, she has used clothing to embrace the fullness of Toronto’s many cultures and communities, wearing a rainbow headdress, sparkles and feathers for Pride; donning a Star Trek outfit for a convention.

In this next phase of her political career, Chow is painting a picture of a leader focused on her agenda of improving housing, transit and city services. And in the face of frightening examples of violent crime— “recent events have shaken our sense of security,” she said in her inaugural remarks — Chow has chosen to project a sense of optimism.

The bold yellow sleeveless dress that she wore on her byelection victory night was echoed by the sunny yellow blazer she wore yesterday. This is fashion deployed for purpose: Chow is dressing to stand out, so she can get her message across. She’s waited a long time for this platform, and she is using everything at her disposal to telegraph her intentions.

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