Skip to content

Business leader keeps Orillia dapper, supports community

'If you’re going to have a business in a small town like Orillia, you need to be out and about in the community,' says Steve Orr, well known for his support of causes, groups

When I first walked into Dapper Depot, a small men’s clothing store on Mississaga Street, I was amazed. It was the vast selection of products that impressed me.

When it comes to clothing and fashion, this small retail establishment seemed to carry just about everything a guy could need or want – from beautiful suits and formal shirts to rugged jackets, caps and jeans.

And then there was the owner, a friendly guy who, if he wasn’t helping a customer pick out the right style or size, was discussing an upcoming community fundraising event.

Even though I’ve become a regular customer over the years, I was curious, and decided to find out more about Dapper Depot. Owned by local resident, Steve Orr, the men’s shop has been a welcome addition to downtown Orillia for the past 22 years.

“I wanted to have a store like the ones I shopped in years ago,” explained Orr, who is in his early 70s. “A traditional men’s wear store that carries everything – shirts, ties, pants and suits, as well as pjs, robes, wallets, jackets, and hats. It’s been working for me for the past two decades.”

Originally from the Weston area of Toronto, Orr began working in retail immediately after graduating from a business and commerce program at Weston Collegiate.

“My best buddy from school was working at Bonita Shoes in the Yorkdale Mall and asked if I would be interested in a job there. We worked together in sales and we did pretty well.”

Before long, Orr was visited at the store by someone who turned out to be a headhunter. He approached Orr with an offer to work with a men’s wear business that was in the process of expanding.

That business was Thrifty’s Just Pants and after accepting a position at Fairview Mall in Toronto, Orr began a career with the company that turned out to be one of the highlights of his life.

Thrifty’s began as a stand-alone store at the corner of Church and Queen streets in Toronto before expanding into shopping malls. Orr explained that Thrifty’s was owned by the Lerman family of Toronto, along with Dylex, one of the largest clothing company conglomerates in Canada, which owned 49% of the company.

“It was the early 1970s when I joined the company and I was making about $90 a week,” said Orr. “Just to give you an idea, back then, the price of a pair of unwashed button fly Levi’s, 14 oz – still made in some place called California – was $9.95.”

New branches began opening up around Toronto “like wildfire,” said Orr, whose job it was to open and manage stores at the Eaton Centre and Yorkdale Shopping Centre, among other locations.

“For some reason, they [Lerman family] really liked what I was doing for them and I was treated as one of the family. Not only was I involved in buying ventures and given opportunities to open and manage new locations, they also included me in many family outings. I remember courtside seats at the Maple Leaf Gardens to watch the Toronto Buffalo Braves. It was a wonderful time.”

The Thrifty’s adventure for Orr ended in the 1980s when the Lerman family decided to sell its business to Dylex. Eventually the Thrifty’s stores were rebranded to Bluenotes.

After leaving Thrifty’s, Orr started up a successful video game business in the Midland area where he and his family enjoyed years of cottaging at Orr Lake (no family relation!).

After a few years of counting quarters and doing lots of fishing, Orr and his family decided to relocate closer to cottage country and pursue Orr’s dream of owning his own men’s wear business.

“That’s my passion and that’s what I think I can do best. I had the confidence to sell myself. And if you can sell yourself, you can sell what you’re selling. That’s how I think I got successful. I could sell without being pushy," Orr explained.

“When we decided to leave Toronto, Orillia seemed to be a natural. We loved the small-town atmosphere, the friendly people and the beautiful waterfront on Lake Couchiching,” he said.

Orr’s entrepreneurial dream started coming together when he met local realtor, Will Davis, who not only found a business space for Orr, but a house for his family. They moved in September of 1999 and Orr opened Dapper Depot a few months later on Peter Street.

“It was tough at first,” Orr admits. “There was Tom’s, Louis and T Bruno’s men’s wear shops in the downtown when I started. Bruno was the king of the castle downtown at that time, so I knew it was going to be difficult. All the high-end suppliers were loyal to Bruno.”

But it wasn’t long before the other store owners retired or closed shop. Orr said the change in competition, along with the sidewalk sale opportunities, was what boosted his business.

“I was offered prime spots during the sidewalk sales, thanks to the support from Robert Lamb and Dave Bourgeois of the DOMB [Downtown Orillia Management Board]. Along with help from my wife and son, we would set up and work all day – the volume of business was unbelievable. That was the heyday of sidewalk sales," reflected Orr. "The streets were just packed with people.”

Within a few years of opening, Dapper Depot moved to its current location on Mississaga Street, where Orr developed a dedicated clientele over the years.

“It’s been my bread and butter for sure,” said Orr, “but what I enjoy the most is getting to know my customers and the local community.”

“If you’re going to have a business in a small town like Orillia, you need to be out and about in the community. If you’re not, you don’t stand a chance.”

Orr soon became involved in local not-for-profit community organizations, the first of which was the Orillia Vocal Ensemble under the leadership of Roy Menagh.

“It’s a pay it forward group,” explained Orr, who sponsored the organization for seven years. “All the money we raised supported non-profit organizations, like a local women’s shelter or other community cause.”

Dapper Depot and Orr have also sponsored the Orillia Concert Band for the past three seasons, not to mention many other music and arts organizations and events over the years. You’ll usually see the front door of Orr’s shop covered in posters letting his customers know about upcoming community events.

Of all of his community support, Orr says he is most proud of this involvement with the Orillia Youth Centre.

Orr was instrumental in helping to launch the Roots North Revisited annual concerts that support the Youth Centre. When working on a fundraising plan, Orr suggested a music festival and instead of creating a new one, had the idea of piggy-backing on the existing Roots North Festival, which is held annually in the spring.

Thanks to support from the directors of Roots North, the idea took off.

“For the past six or seven years, we’ve presented a Roots North Revisited festival in the fall. It’s been fantastic and we’ve had some really exceptional talent. The past couple of years were challenging, but we adapted and are looking forward to being back at Fern Resort in the fall for the 2022 festival," Orr said.

In recognition of his ongoing and generous support to community groups, Orr was honoured as a nominee for Orillia’s Citizen of the Year in 2020. In 2017, Orr was the recipient of the first ever Humanitarian Award from the Orillia Youth Centre.

As for the future of Dapper Depot, Orr is feeling positive, even after a couple of tough years.

“I think all small retail shops are facing challenges with online shopping and the last couple of years have been especially difficult. But I’m confident that my business will be around for as long as I want it to be around," said Orr.

"As long as I am healthy and able, and people continue to like my products and my shop, I’ll be here – to make sure everyone who leaves my shop is 100% happy with what they’ve purchased," he pledged.

That’s good news. Not only will Orr continue to keep his customers looking and feeling dapper, but the community of Orillia will continue to be a huge beneficiary of Orr’s community involvement and support.