Style Bar owner wins top prize at Metis Young Entrepreneurs Symposium

Regan Greenwood opened the Style Bar in Osborne Village in September 2013.
Regan Greenwood opened the Style Bar in Osborne Village in September.

By Brenlee Coates

Regan Greenwood is one of those Winnipeggers we almost lost to glitzier fashion cities like Los Angeles and Toronto several times.
She studied at the Fashion Institute of Design & Merchandising in L.A. before coming home to work at Nygard International.
From there, she moved on to a position at JMJ Fashions Ltd. on Bannatyne until it closed its doors permanently in the Exchange District.
Picadilly Fashions in Toronto then plucked the merchandising expert from Winnipeg, offering her a one-year contract in the fashion capital of Canada.
Luckily, it was toward the end of this contract that Regan started to dream up the business plan for her own store, which she ended up locating right in the heart of our own fashion district, Osborne Village.
For three months after she finished her contract at Picadilly, she stayed in Toronto debating whether or not she wanted to stay and find a permanent position there.
“It was the first time I hadn’t worked since school, so it was a refreshing time,” says Regan.
Though it sounds relaxing, it was over these months that Regan drafted a business plan for her eventual River Avenue store, Style Bar.

Style Bar merchandise at 470 River Ave.
Style Bar merchandise at 470 River Ave.

While she could’ve opened a store in fashion-crazy Toronto, she couldn’t imagine doing it without the help of her nearby family and friends.
“I would’ve done it in Toronto, but I wouldn’t have had the support around me… Me and my mom painted the entire place by ourselves.”
“I’d rather be a big fish as opposed to a small fish in a massive pond,” says Regan.
Regan hoped to bring something “unique to the Village” and perhaps the most standout example of this is the stylish store is relatively equal parts men’s and women’s clothing.

The men's lounge at Style Bar.
The men’s lounge at Style Bar.

The style of the clothing is also slightly more grown up, with lots of chic blouses and casual but elegant dresses.
“My sweet spot is late 20s/early 30s people that are in their career, who’re looking for blouses to wear to work but still want to look funky, and who want to look classy,” says Regan.
Though she is describing her key demographic, she may as well be talking about herself.
“I’m not into the crop tops at this point in my life,” jokes Regan.
Style Bar’s merchandise has a slightly more elevated class to it, but there is still tons of colour – especially evident in the new springwear. Even the men have a section of green basics and interesting print shirts like bicycle print and nautical-themed print button-ups.
Style Bar officially opened in September 2013 and had a busy Christmas season, though like most retail businesses in the city, it suffered through Winnipeg’s worst winter in over a century.
“I couldn’t ask for a better Christmas,” says Regan. “September started off very strong and October and November grew.”
January was hard on all businesses in the area, but by March and April, things were already looking up.
“People are ready to get out – things are warming up,” says Regan. “We’re just gaining awareness now.”
Regan’s business is certainly picking up steam, and gained even more notoriety in late March when Regan won a cash prize for young entrepreneurs from the Manitoba Metis Federation (MMF).
She won the grand prize at a Dragons’ Den-style event, the Metis Youth Entrepreneurs Symposium (YES), walking out with $10,000 to put toward her business.
About $2,500 of the prize goes toward marketing support for the winner’s business.
Regan plans to use the prize money to get her store’s website developed with online shopping.
“The (MMF) have helped me a lot to get my business up and running,” says Regan.
Her prize money will also help her offset some of the costs of hiring two new summer employees.
So far, it is just Regan who works at the store six days a week, and an employee who comes in for her on Sundays.
Besides trying to bring “really good quality for the price” to people in their careers, another major focus of Regan’s business is philanthropy.
Regan held an event for a week starting in late January, where people could bring in gently used denim to be donated to Resource Assistance for Youth, Inc. and receive 40 per cent off designer jeans from Style Bar.
The denim drive ended up accumulating 117 pairs of jeans to clothe youth at RaY.
Regan credits her dad and brother’s entrepreneurial experience for triggering her ambition.
Her father is president of Rondex, a family company started by his father in 1972.
Regan’s brother, Bret, also owns Rondex and is a silent partner for Style Bar.
They help guide her through some of the challenges of owning a business.

Regan with her wall of family photos - and James Dean.
Regan with her wall of family photos – and James Dean.

Ultimately, it was hard work and preparation that helped Regan get to this point and win the Manitoba Metis Federation cash prize – she decided what she wanted to do and where she wanted to do it in April last year; had the location and financing in place in May; and six months later, the place was renovated, painted, merchandised – and open for business.
Style Bar is located at 470 River Ave. in the former Kustom Kulture location. It is open weekdays from 11 a.m. to 7 p.m., Saturdays 11 a.m. to 6 p.m. and Sundays 12 p.m. to 6 p.m. Visit for more information.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s