Wessen Dagnew: The Best Dressed Man in Canada


When Wessen Dagnew talks about “going west” his eyes light up as though he’s envisioning a great journey.

But the westerly walk he’s really talking about is anything but epic. It’s about 700 metres or so, straight across Dundas Street.

He tips his hat at strangers, his cane clucking along the sidewalk like a metronome as he heads towards Yonge-Dundas Square. His daily trek may be less than a kilometre through familiar territory, but to Dagnew, it’s a portal to another world.

At work, he goes by ‘Tony.’ He wears track pants, a hoodie, and dusty black boots. He takes out the garbage and cleans the rooms. In the winter, he shovels the snow.

He’s the definition of nondescript.

But in the square, in the strange simmering soup of downtown Toronto, his dramatic transformation is on full display. He stands like a regal statue, surveying his kingdom behind mirrored shades.

Here, he’s the Ambassador — the nickname bestowed upon him by the friends that hang on his every word and trail him when he walks, as though he were a peculiar pied piper. A wild peacock of the street.

His humble work clothes are a distant memory when he dons one of his 24 custom made suits, from baby blue to blood red. The broom he pushes through the day is replaced by a cane topped with a golden eagle head that gleams in the sunlight. His baseball cap is traded in for a tilted fedora.

He’s visually arresting. You can’t help but wonder what his story is, and, as he’s quick to explain in an exasperated tone, most people create their own.

It’s a story he’s familiar, but not comfortable with. People think he’s a pimp. He can hear the whispers.

“When you dress like this, everybody wants to know how you make a living,” he explains, decked out in a dove white suit and bright red bow-tie.

“I’m not a pimp! I have a job!”

“It used to make me angry but now I’m used to it.”

Before he came to a begrudging peace with being branded a criminal because of his penchant for flamboyance, Dagnew used to carry around his income tax returns.

Like a war-time gangster who diligently packs a gat, he wouldn’t leave home without government-endorsed evidence of his employment.

He would pull the slips out at the slightest sideways glance, eager to prove he was a hard-working man, not a criminal.

“Some of them I showed my income tax return, how much money I make at my job, and still they call me pimp!”

“They would say, ‘How come we don’t see you with girls?’

“Because I’m not a pimp!”



Dagnew’s outward appearance on his daily walks belies his ascetic existence.

He’s been working at the same rooming house near Queen and Sherbourne streets for the past 17 years, seven days a week. Many of the residents are plagued with drug and alcohol addictions and mental health issues.

“It’s good to help people,” he says. “Most of them, they are good people.”

He lives at the rooming house, in a shoebox-sized room that can barely accommodate his mattress, a small dresser and the clothes rack where his suits hang.

He’s up every day at 5:30 a.m.

“I don’t drink. I don’t smoke, no cigarettes, no beer, no wine, since I was born, never,” he insists. “My priority is my work.”

The spry 61-year-old even had to tone down his one admitted vice, switching from regular Coke to diet after he developed diabetes.

He laughs when he imagines people conjuring images of a fast-living street hustler when they see him decked out.

“I’m clean like a child, I’m a hard working guy. But they judge you the way you dress.”



Before he came to Canada in 1991, Dagnew was a teacher for 17 years in his native Ethiopia. Even as a young boy he had an aesthetic flair. “I used to love to dress up, he explains. “It grew up with me.”

But his affinity for unique threads became a full-blown passion after he spotted an album cover near St. Lawrence Market one day.

“This group they dressed all in blue, six of them, everything, baby blue. I said ‘why don’t I have this kind of suit?’ “

“I went to Fabricland. I bought the material and found an Italian tailor … and I told him for my first suit, I want baby blue.

“Then I walked around and people called me pimp. I said ‘I’m not a pimp.’ I tried to convince them. But they told me you’re a pimp if you dress like this.”

“The police stopped me several times, ‘What do you do for a living?’ ”




Dagnew has spent the morning cleaning nearly 45 rooms. It’s time for his lunch break, and the first of his two daily walks.

Like a meek Clark Kent slipping into a phone booth and emerging as a muscled superhero, he enters his room as Tony and emerges as the Ambassador.

“It makes me very happy when I dress like this,” he insists. “I enjoy it … I work seven days a week, but when I come out I’m like a king.”

But his joy is tempered because his passion has also burdened him.

“What I didn’t know, is that when you dress like this, people call you pimp,” he adds with an endearing naivety. “I didn’t know.”

“I like people to know that I’m a hard working guy.”

“Don’t judge a book by its cover,” he adds, his lower lip trembling. “You don’t know what is inside.”