Although born in Kraków, Poland, Werbowy holds both Canadian and Ukrainian citizenship. When she was three years old, Werbowy's Ukrainian parents moved to Mississauga, a suburb of Toronto, Ontario, Canada. She has a brother named Orest and sister Oksana. At age fourteen, Werbowy was 5'11", willowy and sporting braces. She attended St. Sofia Ukrainian Catholic Elementary School and Cawthra Park Secondary School as a visual arts student.
She is an avid sailor and spent three months in 2008 sailing across the Atlantic Ocean and the Mediterranean Sea. In 2011, she embarked on a two-month expedition from Guatemala, travelling around Central America to Costa Rica.
Werbowy had never seriously considered modeling, but found herself launched into the business after meeting a schoolmate's mother who headed Toronto's Susan J. Model & Talent Management. At age 14, Werbowy won a national modelling contest.
After switching to Elite Model Management, Werbowy landed several prominent bookings in Canada but achieved little international success. Werbowy lived in London and Greece, where she did not find much work. Her first runway season was disrupted and her bookings canceled after the 9/11 attacks in New York City. After a disappointing eight months, Werbowy returned to Canada. She gave modeling a final shot as a means to fund her art school education. "I returned to New York, met my agent and the next day I had an exclusive deal with Prada. From then on it was all a bit of a blur."
When the Elite Canada's head scout, Elmer Olsen, started his own agency, Werbowy followed and her career began to flourish. Within a few years, and under the guidance of International Management Group (IMG), Werbowy gained a foothold on the international modelling stage.
Though she relinquished the world's No.1 runway model status to new "it girls", Werbowy holds the record for opening and closing the most shows in one season. To date, Werbowy's clients have included Lancôme, Prada, Yves Saint Laurent, Pepe Jeans, Roberto Cavalli, Gucci, Hermès, Valentino, David Yurman, Missoni, Versace, Louis Vuitton, Oroton and Chanel. In her first season, Fall/Winter 2003, Werbowy captured two of the modeling world's most coveted assignments: the cover of Vogue Italia, thrice (in July, August and October), and Prada's Fall/Winter ad campaign.
Photographed by Steven Meisel, she was presented on the September 2004 cover of American Vogue as one of the "Models of the Moment". In July 2007, Forbes listed Werbowy as the ninth highest-earning model in the world after Karolina Kurkova, Natalia Vodianova, Carolyn Murphy, Alessandra Ambrosio, Adriana Lima, Heidi Klum, Kate Moss and Gisele Bündchen. Her earnings between June 2006 and June 2007 were in the order of $3.5 million.
On September 6, 2008, she was inducted into Canada's Walk of Fame. She is the second Canadian model, after Linda Evangelista, to have a star on the Canadian Walk of Fame. Earlier that year, Werbowy launched a three-piece makeup collection by Lancôme for Sephora. The proceeds went to the Vik Muniz charity Centrao Especial for underprivileged youth in Brazil. Werbowy was one of the faces on one of the fourteen covers of V magazine September 2008 issue. Each cover boasts a head shot of a famous model, either from the new crop of leading models (Agyness Deyn, Lara Stone, Natasha Poly, Anja Rubik, etc.) or the supermodel era (Christy Turlington, Naomi Campbell, Eva Herzigova). The covers were photographed by duo Inez van Lamsweerde and Vinoodh Matadin.
Vogue Paris declared her one of the top 30 models of the 2000s.
Werbowy has had conflicted feelings about her professional life. In the September 2008 issue of Fashion Magazine she was quoted as saying:
"I've had a lot of mixed feelings about what I do ... A lot of the time, I feel like I'm part of the problem when it comes to all the superficiality and vanity that impacts the way girls grow up".
Werbowy was photographed alongside Lara Stone and Isabeli Fontana in the 2009 edition of the Pirelli Calendar photographed by Peter Beard and was also featured in the 2011 edition photographed by Karl Lagerfeld.
She ranked No. 6 on Forbes' "The World's Top-Earning Models" list, with estimated earnings of $4.5 million between May 2010 and May 2011.
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