Winnipeg isn’t going to be the first name that comes to mind when you associate fashion with a city. Places like Vancouver and Montreal tend to get more attention in that regard.
But despite earning a six-month scholarship with the brand 3sixteen in New York City, Chris Watchorn made the choice to come back to his home city.
“I feel like Winnipeg is a very friendly city. It’s also a smaller city, and I feel like it’s easier to spread the word brand wise,” says Chris, owner and designer of the Oak + Oar fashion brand. “I have a lot of good friends, a lot of good people here, a lot of good business like Tub, and people who are really supportive.”
While in New York, Chris was able to experience the many facets of running a clothing brand, and he used that experience to start up Oak + Oar. The brand launched in the summer of 2012.
Since returning to Winnipeg, Chris has been working full time with FXR Racing in Oak Bluff. After five years of working there, Chris felt that it was now or never if Oak + Oar was to reach its potential.
“I’m not getting any younger and I feel like I’d regret not going for it now. I’d hate to have looked back in 10 years and said ‘maybe that could have been something’. So I quit there, I’m self-employed now doing Oak + Oar full-time. I have another brand called Olé denim that I’m doing with two friends from Saskatchewan that we just launched last week which is getting carried in a few stores in Canada. Between those two projects I’m keeping pretty busy.”
Two of Chris’ biggest passions are garment design and cabin life, so the choice to combine the two was a simple one
“For me, it mixes two hobbies or two passions. I love going to the lake. My parents have a place in the Whiteshell that I tag along to. There’s just something about escaping there. I feel creative,” said Chris. “You don’t have the distraction of the internet and phone, so you can focus and do design stuff. It’s a pretty inspiring place to be, and I thought if I can mix my two hobbies and make a business out of it, it’d be pretty cool.”
From that mindset, the Oak + Oar brand was born, with Olé building off some of the following that Oak + Oar had developed to help the young brand grow quickly.
“I wanted to build off a little bit of a following that I had with Oak + Oar so Olé had a little bit of traction to hit the ground running. That was a project that I started with two friends, Ryan Mack and Dallas Siemens. They both went to the University of Saskatchewan and have business backgrounds. For me that’s allowed me just to focus on the design aspect of the business.”
Oak + Oar is currently being sold in two Winnipeg locations, at Tub and Stylebar, while Olé is sold at Normandy Shoppe in Winnipeg and three locations in Saskatchewan.
Big League Help
Chris has benefitted from the social prominence of some of his clientele, with many players of the Winnipeg Jets seen sporting his gear.
“That was pretty huge and I think that if that didn’t pan out as early as it did I might not be at the point that I am now. If you have someone wear that and show up on social media it helps out a lot.”
Chris’ friend and barber, Dru Barrow from Hunter & Gunn, had attended an event where Chris had a popup shop and bought some of the Oak + Oar products. Dru happens to cut hair for several members of the Winnipeg Jets, and when defenceman Mark Stuart had gone in and seen Dru wearing it. Mark inquired about the brand, and has since bought items, becoming a regular customer and even contributing to help design a belt with Chris and Vancouver based leather designer Ken Diamond. They decided to do a pop-up evet, and to Chris’ surprise, most of the Jets roster showed up.
Taking The Leap
Looking back, Chris says that taking the plunge into his own business as soon as he came back from New York might have been better than waiting to see if Oak + Oar would take off on its own, encouraging others to go take the risk now rather than regretting it later.
“I would say just go for it as soon as you can go for it.”