Frank McKenna (left) poses for a photo with, CEO of the Hartt Shoe Company Andrew Bedford.

In The Shoe Guys, we bring you insight and experience from some of the most prominent figures in business, politics and beyond. We talk business, we talk style, we talk shoes. For the first article in The Shoe Guys series, we caught up with Frank McKenna, Deputy Chair of the TD Bank Group and former Canadian Ambassador to Washington.

When you spend your nine-to-five around some of the world’s most powerful, successful and stylish people, it’s important to look the part. Few know this better than Frank McKenna.

The business and political powerhouse has made his career navigating the waters of international diplomacy and political debate, rubbing shoulders with Presidents and Prime Ministers alike.

McKenna, formerly the Canadian Ambassador to the United States, is the Deputy Chair of the TD Bank Group, a position he’s held since 2006.

“I’m number two here at the bank,” said McKenna from his office in downtown Toronto. “We’ve got about 85,000 people working worldwide... Our asset base is worth well over one-trillion dollars and we make close to 12 billion dollars a year.”

Some of McKenna’s responsibilities include managing investor relations and presenting at many of TD’s public events. These events take him all over the world.

“I deal with a lot of Premiers, Governors, Presidents and Prime Ministers... I host a lot of events for the bank with celebrities like Wayne Gretzky, Kyle Lowry or Jose Bautista,” said McKenna.

In his role as Canadian Ambassador to the United States, McKenna dealt with powerful people on a daily basis.  

“Being Ambassador in Washington was a very, very rich experience and it was one of those jobs where there wasn’t a day that went by when you didn’t feel like you were right at the centre of the universe drinking from the big firehose, because all of the issues of the world go by your doors,” he said.

When it comes to style in business, McKenna is a sharp dresser, adding that style has had a big impact on his professional life.

“There’s no doubt about it. You have to project an image whether in business or in politics… You’ve got to look the part,” he said.

Having spent the majority of his career around well-connected, smart and sharp-dressed individuals, McKenna says that - in terms of style - one has stuck out above the rest. McKenna’s style icon is none other than former U.S. President Bill Clinton.

“He just loves to dress in beautiful shirts and suits… He would probably be one of the most stylish people I know,” he said.

During his time as the Canadian Ambassador in Washington, McKenna says it was extremely rare when a day would go by without meeting with a leader in business or politics.

“I would have stunningly good opportunities on a daily basis to be at the white house or up on capitol hill or to meet interesting people, whether they are CEOs from Canada coming in, or CEOs from the U.S., or Senators, or even the President.

First impressions set the tone in any relationship. In the case of how McKenna became friends with former U.S President George W. Bush, it was getting late and the two were stuck at a formal function with hundreds of diplomats. To make matters worse, the world series was on.

“It got a little boring for me so I got up and started sneaking out the door and he (President Bush) said ‘McKenna, where ya goin’?’ I said ‘Well, the world series is on. I want to catch the end of the game.’”

President Bush, recognizing that McKenna wasn’t just another diplomat, but someone who you can relax around, said “I’m right behind ya.’”

“Out of a lot of those interactions, some great friendships were created,” said McKenna.

When asked about the Hartt Shoe Company, McKenna spoke of the brand fondly.

“My experience with Hartt goes back to when I was a young politician and I got measured up for it and wore the product and wore it proudly,” he said. “I absolutely love Hartt shoes.”

Recently, McKenna entered into Robert Simmonds in downtown Fredericton to meet with Hartt CEO Andrew Bedford. McKenna was fit for a new pair of Hartt shoes from our Heritage Collection.

He chose the Westmorland, a brown, wingtip derby with a contrast sole. The Westmorland can hold up in boardroom meetings and business travel. He also chose a black tassel loafer, which we have named the McKenna in his honour.

Like all shoes in the Heritage Collection, it features Goodyear-welted construction, premium vegetable-tanned, french-calf leather, leather sole and a stacked leather heel.

“It always makes me feel good knowing that I’m wearing something unique and that’s also going to last me a long time,” said McKenna.