POP CULTURE | A Conversation with


Fredericton’s Jeff Alpaugh approached his appearance on CBC’s Dragons’ Den the way he approaches most things in life. He knew exactly what he wanted, and he went for it. But that wasn’t always the case. When asked why he started The World’s Most Dangerous Dress Shirts, Alpaugh remembers his first experience buying a suit. “I was expecting to look like James Bond … until I looked in the mirror and realized that was definitely not the case,” he chuckled. “But the salesman convinced me it was the right suit for me.” Now, in retrospect he recognizes that the suit was easily 5 sizes too big for him. Then he got a job in fashion where he got a suit that fit properly, and he still remembers the transformative feeling of confidence it gave him. “It was such a positive force in my own life that when people came in looking for a shirt or a suit – I was so excited to give them that same experience.” He continued his career in fashion with industry leader Harry Rosen in Toronto, where he gained extensive experience. “Customers were always looking for what’s new, but nothing was ever really new or wild.

The Birth of an Idea

Traditionally, clothes are made in the East and sold in the West,” Alpaugh explains -“that’s just the way the fashion industry works. People who buy fashion for brick and mortar stores are buying two or three seasons in advance, basically hoping that’s what is going to be in fashion.” He went on to explain that those shirts are made in huge batches, because they have to fill shipping containers to ship overseas. “But with the advent of the internet, that just isn’t necessary anymore. If you make the shirts customized by order, you don’t have to mass produce.

I thought to myself, if the customer is willing to pay these prices for off-the-rack-clothes, why can’t we just let the customer decide what they want, and order just that shirt? Why order hundreds of shirts knowing we will only sell a portion of them? It’s good for the business – we only have to make that one shirt. It’s good for the customer – they get exactly what they want. And it’s good for the environment because there’s no waste!

This gave birth to the idea of Jeff Alpaugh Custom in 2016. Jeff and his wife Emilee have been running the business while working with the military this whole time. That all changed this year, as they grew the business and now commit to it 100%. “I left the army earlier this year, and we expanded into our new building at 364 Victoria Street in downtown Fredericton. In January, we did a tour around the country to do some private measuring events, and then had our grand opening in the new store in February.”

Dragons’ Den

When asked about their experience of being on Dragons’ Den, Jeff explains that the process is a lot harder than it looks when watching it on TV. The timeframe from applying to be on the show to when the episode airs is well over a year, so when figuring out the pitch they wanted to make, Alpaugh really had to think forward. “There are a lot of companies from New Brunswick who have seen success on Dragons’ Den, so we did our homework, and worked hard to figure out what we wanted to ask for.” Jeff Alpaugh Custom was only 8 months old when they made the pitch but was almost 2 years old when it aired in November of 2017. “We had our priorities set – first, we wanted to be on TV. They do the auditions, then invite 160 people to pitch in front of the Dragons over 3 weeks, then select 100 to be on TV. So, we got that. Second, we wanted to look good on TV, and I hope we did that. Then third, we wanted to make a deal. But that really was our third priority.” Emilee adds “We also considered which Dragons we would want a deal with and focused our pitch on Michele Romanow and Mike Wekerle. Michele is strong on the ecommerce side, and Mike would understand and live our brand.” And in the end, as you can see on the show, they did get offered a deal from the Dragons who they wanted to work with. To see Jeff Alpaugh’s episode of Dragons’ Den, visit cbc.ca/dragonsden/pitches/jeff-alpaugh-custom.

The Portfolio

Jeff Alpaugh Custom has expanded the product line far beyond the original Most Dangerous Dress Shirts. As you can see on www.jeffalpaugh.com, you can order:

  • Dress Shirts (men’s, women’s and kids)
  • Suits
  • Blazers
  • Dress Pants
  • Vests
  • Chino Pants
  • Be Dangerous T-shirts
  • Dangerous “Barkspoke” dog collars
  • Dangerous Socks
  • Bomber jackets
  • Cufflinks
  • Pocket squares
  • Ties

What’s next?

“In 2019, we are opening our second store in Waterloo, Ontario where Emilee and I went to University. We are excited to bring our Fredericton business to Ontario.” The Dangerous portfolio will also continue to grow, as they recently started offering dress pants, and look forward to working with denim soon.


So, what do the couple who created The World’s Most Dangerous empire enjoy at the end of the day? “We often like a glass of the Macallan, paired with Brie and crackers” said Jeff. “Five years ago, Emilee got me Scotch rocks as a gift to play on my ‘James Bond factor’ and I love them. Few things make me happier than eating an entire wheel of heated Brie in one sitting, while sipping on scotch.” It doesn’t get more dangerous than that.