Douglas McCorkle’s financial career started with six numbers.

At 22, he was working at Canada Post and won the lottery. He split the grand prize with five other winners, and each walked away with about $49,600.

Two years later, he had to borrow money to buy a car. “I blew through that lottery winning because I didn’t have a clue what money was worth,” he says.

He realized he needed to change his financial habits, and wanted to help others learn from his mistakes. So he got licensed, and has been a financial advisor at HollisWealth Advisory Services Inc. for 25 years.

McCorkle continues to share his story with clients, saying, “if I’d taken those winnings and bought Berkshire Hathaway, you wouldn’t be having this conversation with me because I’d be independently wealthy and living some-where abroad.”

And while business is steady, McCorkle notes he has challenges: specifically, his personal style. “When I look at myself in a mirror, I just feel frumpy and incomplete,” he says. “I did a lot of weight training in my younger days and I’ve let that go, so my clothes hang.”

He adds that he and his wife, who also works at the firm, have to stretch the household clothing budget between the two of them, as well as with three daughters.

He finds style challenges can affect his client conversations. “If you look good, you feel good. I want to look and feel professional and confident, because if you’re feeling confident, you’re more effective as an advisor.”

Meeting the expert

When McCorkle reached out to Advisor Group, we had to help. So we set up a meeting with Sagit Vyner, a personal shopper at Holt Renfrew in Toronto.

She says, “Within a few minutes of meeting you, someone already has an idea of what you’re about—if you’re successful, and if you’re the person they want to be taking care of their investment portfolio.”

Vyner adds when you look polished, investors will translate that look into you being in control of your life. And they, in turn, will put you in control of their investments.

While chatting with McCorkle, Vyner learns one of his style challenges is that, like many men, he’s actually colour-blind.

“I’ll walk downstairs and if my wife gives me ‘the look,’ I’ll turn around and go back up and change because I know I don’t match,” he says. To cope, he often will only buy dark-coloured clothes. But Vyner says being colour-blind shouldn’t deter you from playing with colours and patterns.

To help people in his position, she sews tags into their clothing to identify the colour of the shirt, jacket, pant or tie.

Her style evaluation starts with questions about a person’s life, including what he does for a living, if he’s married with children, and what he does in his downtime.

“Style has a lot to do with someone’s personality, so it’s essential to get to know them. Doug is fiery, funny and whimsical, so I think his clothing should be reflective of that.”

Vyner factors in McCorkle’s height (5’4”) and colouring, noting his tanned skin tone allows him to get away with almost any colour, from dark blues to vibrant purples.

“If someone is shorter in stature, you have to work the proportions accordingly. For instance, you have to find a sports jacket where he’ll just be able to cup the end of the jacket with his fingers. Also, the pants should be narrower to give him more height.”

Watch Sagit Vyner, personal shopper at Holt Renfrew, give advisor Doug McCorkle key fashion tips.

Makeover snapshot

Doug’s challenges

  1. He’s colour-blind.

  2. His clothes don’t fit.

  3. He wants an updated look.

What the expert says

  1. Sew tags into your clothing that have the colour written on them.

  2. Take your clothes to a tailor if you’re budget-conscious. If you can splurge, buy custom-fit clothing.

  3. Invest in the latest accessories and don’t be afraid to play with colours and patterns.

Doug’s reaction to his makeover

“It’s been almost life-changing. I’m sitting taller in chairs. I’ve gotten more work done this week than in any week prior. I’m focused, and I actually feel different now that I’m dressing better.”

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