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 somewhere 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.”

McCorkle adds he always buys clothing off the rack. Shirts that fit in the neck are loose everywhere else.

Vyner isn’t surprised. “For someone like Doug, fit off the rack will be a challenge, so custom tailoring is a worthwhile splurge.”

But if you want a budget-friendly option, she suggests investing in some tailoring.

“You can take an average off-the-rack suit and make it exceptional if it fits properly. It has to fit well across the back, and the pants shouldn’t be too wide.”

Additional cost-effective options include accessories, which she says can easily update an old look. This includes colourful pocket squares and ties, or a belt that’s not black—navy and wine-coloured are the latest trends.

“Buy on the highest end of what you can afford,” says Vyner. “You won’t be disappointed by its wearability and you’ll get the most mileage out of it.”

For instance, if your budget is $2,500 for a beginner wardrobe, she’d allocate $1,500 for a single suit, instead of $500 for three suits.

“One high-quality suit will outlast three cheaper options,” she says.

Then she’d take the remaining $1,000 and buy several shirts and ties, which will give you various looks.

And this is what she suggests for McCorkle. During their meeting, she shows him that, even if he has the same jacket, he can create a whole new look simply by changing a few items.

For instance, he can put on a different coloured shirt or belt, a patterned tie, or add in a pocket square.

5 fashion tips for businesspeople

  1. Treat your wardrobe like any other investment. You invest in your home by fixing the roof or updating the kitchen so that it keeps its value—you have to do the same with your wardrobe. Give yourself a monthly or bi-annual allowance, and get the pieces that’ll give you the most benefit for the long term.
  2. Never underestimate accessories. They’re what makes you stand out, and helps clients remember you. So you’ll be top of mind when they need an advisor.
  3. Grooming is important. If your hair is a mess and your nails are different lengths, then no matter what you wear you’ll look less refined. And clients will think you don’t have enough time to get organized. You want people to see you have your whole life under control.
  4. Make sure you have the basics first. You can’t build a closet on gravy pieces. Basic workwear is a dark-coloured suit: ideally a three-piece for men and a skirt suit with pant option for women. Get the best quality you can afford so it lasts. Then buy accessories that reflect your personality. For women, it could be a printed dress or brightly coloured pumps. For men, it could be patterned socks or ties.
  5. Take care of your shoes. They don’t have to be top of the line, but they should be polished. In the winter, remove salt stains. For women, make sure heels are intact. See a cobbler regularly because, when you meet with clients and sit down, they’ll notice your shoes.

Source: Sagit Vyner, personal shopper, Holt Renfrew

Before & after

You can take an average off-the-rack suit and make it exceptional if it fits properly. It has to fit well across the back, and the pants shouldn’t be too wide.
—Sagit Vyner

What we noticed
Get the look!

Follow up

We checked in with McCorkle one week later. He was enthusiastic about his experience, adding that clients and staff have noticed the change, and a new client was impressed by his style.

“It’s been almost life-changing. I’m sitting taller in chairs. I’ve actually 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.”

And he’s taken the style tips to heart. He’s thrown out several ties and worn a shirt and tie to work each day. He’s also scheduled a meeting with his tailor to have his professional wardrobe redone.

“I’ve begun noticing others’ clothing as well and can pinpoint any problem areas they have.”

Phil’s style tips

Douglas McCorkle had the opportunity to meet Philip Porado, director of content, Advisor and Financial Services Group, who’s dispensed many a style tip to his peers. McCorkle was a great sport as Porado analyzed his current wardrobe and provided constructive criticism by telling him whether to “toss, tailor, or keep.”

Here are several highlights:

  • Three ties were stained, torn and otherwise worn past their expiry dates, and were tossed. TIP: Look for wear and tear, especially where a jacket button may rub against the tie.
  • All of McCorkle’s shirts and jackets needed to be tailored at the shoulders and waist to remove excess material. TIP: Wearing clothing that’s too big can make you look bulky, so ensure yours are well fitted.
  • One pair of dark jeans and a half-sleeved shirt were deemed unsuitable for the office, even on casual Friday. Porado kindly suggested McCorkle save them for a kid’s soccer game. TIP: If you’re seeing clients, look professional—regardless of what day of the week it is.
  • McCorkle’s dark pocket square was considered too somber for his vibrant personality. TIP: Don’t be afraid to have fun with accessories.