A Quick Q&A with Donovan Bailey

Those lucky enough to witness Donovan Bailey in his prime remember an athlete who embodied peak performance and world-record excellence — not just for Canada, but for the sport of athletics itself.

At the 1996 Atlanta Olympics, Bailey claimed gold in the men’s 100-metre sprint, earning the title of the world’s fastest man, before adding a second gold as part of Canada’s 4x100m relay team.

Today, Bailey remains an active and influential figure in the Canadian and global athletics community, inspiring and mentoring the next generation of sprinters.

We caught up with Donovan Bailey to talk sport, style, and speed during an in-store styling session.

Q: Did you have any sporting heroes growing up?

 A: Muhammad Ali and Michael Jordan were my biggest heroes. Ali wasn’t just a fighter; he was a global icon who carried himself with confidence and conviction — both in and out of the ring. Jordan, meanwhile, set the standard for excellence, discipline, and style on and off the court. Both inspired me to chase greatness and to understand that how you present yourself is part of your legacy.

Q: Who is your biggest style inspiration?

 A: I’ve always admired the timeless elegance of Giorgio Armani and Tom Ford. They both understand the power of tailoring and how the right cut can make anyone feel like their best self. Their work has shown me that style isn’t about chasing trends; it’s about making a lasting impression.

Q: When you step into Harry Rosen, which brands do you gravitate towards?

 A: I tend to choose pieces that suit my body type and lifestyle. As a former sprinter, I still have an athletic build, so fit is crucial. Harry Rosen effectively curates brands that find a good mix of performance and sophistication.

Q: How important is having a sense of personal style to you?

 A: Essential — it’s part of my global brand. As an athlete, an entrepreneur, and a public speaker, I’m constantly in the spotlight. Personal style is my way of communicating confidence and professionalism before I even speak. It’s not about being flashy; it’s about consistency, quality, and presence.

Q: Do you prefer shopping in person or online?

 A: I prefer the personal shopper experience. There’s nothing quite like having someone who knows your measurements, understands your taste, and can recommend pieces that enhance your wardrobe. It makes the process smooth and ensures every piece feels purposeful.

Q: What’s one wardrobe error that athletes often make?

 A: Athletes sometimes wear fashion that doesn’t suit their body type — especially when it comes to muscle or curves. Fit is everything. No matter how expensive or trendy the clothing is, if it doesn’t fit properly, it detracts from the overall look.

Q: Do you have any style dos and don’ts?

 A: My biggest “do” is to wear what truly fits you — physically and personally. A great outfit should enhance your presence, not fight against it. My biggest “don’t” is chasing trends that don’t suit your frame or personality. Style is about authenticity; when you’re true to yourself, it shows.