Portrait
Ahead Of The Curve
by Gavin MacDougall, Photography by Steve Pomerleau

Ari Freed and Dan Orman keep
Freeds of Windsor two steps ahead of fashion’s trend

As the camera repeatedly clicked before them, the two gentlemen clad in designer jeans and Affliction t-shirts continued to follow the directions of the photographer and a nearby assistant. Unshaven and cool, in a hip sort of way, the pair presented the look of a couple buddies you might run into at a Spits or Wings game. Or maybe a concert or a bar on a Friday night. Actually, just about anywhere for that matter. This much was certain: they didn’t look like the way they’ve come to look like for literally thousands and thousands of Windsorites over the last twenty years.

That’s to say, they didn’t look like Ari Freed and Dan Orman. Thanks to decades of being arguably the region’s most active and prominent advertiser, Freeds of Windsor’s Ari Freed and Dan Orman – much like their fathers Gerald Freed and Alan Orman before them – are as recognizable as anyone in Windsor and Essex County. But that recognition has almost always been while wearing a dapper suit or dress jacket and pant, with smiles at the ready. But never, never like this.

Mission accomplished then. But more on that a bit later. How do you go about changing a Windsor retail institution? Better yet, why would you want to? To ask that latter question though is to miss the whole point of what has made Freeds the success it is today, and really has been since family patriarch Sam Freed – Orman and Freed’s grandfather - opened his little shop in Olde Walkerville back in 1929.

“In our business and industry, if you stand still you lose,” says Orman, point-of-factly. “The fashion industry is constantly changing and you have to be one step ahead of the curve to succeed in it. That’s something our grandfather understood in his time and it’s certainly something our fathers have understood over their careers. I think Ari and I, and our management team, continue to recognize and appreciate that need for change to this day.”

Indeed, just as it has throughout its near 80-year history, Freeds of Windsor is changing again. And what better way for the co-owners to introduce an element of that change than to ‘strike a pose’ in the very duds their new department will be featuring. Welcome to the latest department in the world of Freeds: Just Jeans – a new 15,000 sq. ft. jeans and casual wear department, located in a mezzanine section of the Ottawa Street store, that is as dazzling a visual experience as it is a bevy of new styles and fashion trends. The line-up of apparel? Well, let’s just say it’s about as far away from what most have come to know Freeds by over the years. Featuring an eclectic array of jeans, t-shirts and other casual wear, the department offers customers “more than 50 different ways to wear jeans," according to Orman.

“This is without question the newest and most exciting thing we’ve done in the past fifteen years,” agrees Orman. “Is it different from what most people have come to expect from Freeds? In many ways yes, but at the same time Freeds has always prided itself on being one step ahead of the fashion curve and this new department is no different. It’s really become a jeans kind of world. Corporate casual in the workplace is as popular as ever and you’re really seeing an ever-increasing acceptance of jean-wear for events that previously would have demanded a casual slack or Docker-type ensemble. Jeans are where it’s at right now. People want them for so many different means right now.”

Contrary to popular belief, taking the reins of a successful family business the size, scope and with the tradition and history of Freeds is no slam-dunk, guaranteed ticket for success. As Orman and Freed can attest, their family business probably has to work twice as hard now to ensure the continued success it has enjoyed over the past eight decades. Oh yeah, then there’s that whole responsibility of protecting the legacy. No pressure there, right?!

Fifteen years ago, just around the time he and Freed were in the process of taking over the day-to-day reigns of the business from their fathers, Orman jokingly commented to a friend that he had come to understand the true meaning of pressure, which he cracked was making sure he and his cousin didn’t undo in a few years what their fathers and grandfather had spent the better part of seven decades building! And who would argue that point.

“That pressure is still something we face every day in this business,” says Orman, when reminded of that long-ago uttered comment. “I think those who’ve taken over family businesses understand that things can unravel a lot quicker than they came together. We look at the legacy of this business with a great deal of pride, which is why we make an effort every day to duplicate the values and traditions that our grandfather and fathers put into this business. Are we afraid of change? Absolutely not. Like I said, it’s part of our business. But one thing about Freeds that will never change are those core values that have been passed down to us. Things like treating our customers and our staff with the utmost respect, and really caring about the people we work with and the people we serve.”

If ever there was a retailing institution in Windsor and Essex County – or for that matter, in all of Canada – Freeds of Windsor is it. Literally tens of thousands of these kinds of scenes have played themselves out at the store over the years: a young lad, with mom and dad accompanying, picking out that first-ever suit; perhaps for graduation or a relative’s wedding. The new office worker, fresh from landing his first job, using his initial pay cheque to craft a new wardrobe. Or the repeat customers – the list of which by now would likely rival the size of a small phone book – updating their clothing collection at the place they, their fathers, and their grandfathers have shopped for years.

And yet, in spite of having branded itself into the collective minds of shoppers across Southwestern Ontario and even into Southeastern Michigan as the suit place, Freeds of Windsor is continuing its selfdescribed “never-ending evolution.” Now more than ever, Freeds - as its owners are quick to tell you – is more than a “suit place.” In fact, it’s always been more than just a place for suits; even when it seemed all Sam Freed sold was suits.

“Freeds has been and always will be about providing a great shopping experience for our customers,” says Freed. “And a huge part of that experience we’ve come to realize over the past twenty years that is so important to our customers is continually providing the newest and freshest fashions the industry has to offer. It really is a philosophy that has been part of our growth since our grandfather opened Sam’s all those years ago.”

When Orman and Freed began their careers with the family business, Freeds was still regarded as that “suit store.” But when Chrysler and other local businesses went with the corporate casual approach to apparel in the late eighties and early nineties, Freeds had to adapt. “We had to find a new way to portray our store. That’s when we realized we had to be more than a suit store. Suits were still going to be a big part of what we did – and they have remained so – but we knew we had to be so much more than that. We want our customers to see that this is the kind of place, and the kind of shopping experience, that can accommodate all their apparel needs. That’s why at Freeds, people will now find everything in our store on sale every day of the year.”

Orman says this kind of strategy is something the fashion industry essentially demands of its best players, and why Freeds has consistently “re-invented itself” every five or six years.

“Like many industries, fashion is pretty non-forgiving for those who stand still,” he says. “It truly is a ‘stand still and the world will pass you by’ kind of thing. That’s why we’ve always made a point to expose ourselves to all kinds of fashion elements. The only way to know what the consumer wants is to understand what kinds of things are out there.”

Orman recognized this early on in his career at Freeds. Just three days after graduating from York University in 1984, he went to work for the family business, and brought with him the influences he’d seen from living in Toronto for four years.

“I was exposed to so many different fashions while in Toronto,” says Orman. “There were some crazy different clothes being worn by people in that city, but I felt like it was only a matter of time that people in Windsor and Essex County would adapt to those kinds of fashion trends as well. I was fortunate that my dad allowed me the freedom to explore these kinds of things for the store. I guess you could say he gave me enough rope – I could sink or swim with these ideas I was bringing to the store.”

One of these new ideas in particular proved to be a huge success for Freeds, and was a harbinger of things to come as far as the store’s willingness to adapt to changing fashion trends.

“At that time, the Roots line of clothing was sweeping the country but there was no one in Windsor selling it,” says Orman. “We introduced the brand to Windsor and made it a very high profile part of the store. It was also during that time that the whole ‘Miami Vice’ look was really gaining speed. Clothing like that was something Freeds had never endeavoured to carry, but my father gave me the opportunity to develop those kinds of lines for the business, and I think that helped foster this philosophy of never standing still and always looking ahead as to what the (fashion) industry had coming next. It was definitely something new for us: full departments of casual and sportswear type clothing. Looking back, the contrast between all of those formal suits and what the Roots and Miami Vice look brought to the table must have seemed startling to some, but it was the right thing to do for our business.”

In many ways, Freeds’ ability to “change with the times” is what sets it apart as a dying breed among Canadian – and really, North American – clothing retailers: changing store looks and merchandising techniques on a dime, adapting new product and pricing strategies, and always, always doing what’s best for its customers, while never losing its heart and soul business values.

“I think it’s true that our store and business is very much a dying breed,” says Orman. “Because our ownership and management team are so visible and so involved in store operations on a day-to-day basis, we have the ability to change what we’re doing very quickly. That’s something the ‘big box’ places can’t really do. If something doesn’t work for us, we change it in a hurry. Over the years, we haven’t been afraid of making those changes, and we never will be. That philosophy has been a hallmark for Freeds over the years. We pride ourselves on being cutting-edge marketers and merchandisers. Have we made some mistakes along the way? Absolutely, but in each instance we were doing what was best for our customers.”

Today, with an added emphasis on low prices and continued huge selections, some might think Freeds has completely gone the way of the discount store, but both Freed and Orman have an interesting take on that.

“We’ve always been a promotional store, with a heavy emphasis on providing great pricing for our products,” says Freed. “Anyone who knows even a bit about Freeds, or has shopped here, knows that’s always been a big part of what we're about. But we’ve been fortunate to have developed outstanding relationships with a vast variety of top-name suppliers, who value our business and give us great deals that we can then pass along to our customers. Does that make us a discount store? Well, I guess you can call it what you want but we like to think that we’ve always provided a premium shopping experience at pricing that people just can’t find anywhere else. “

Orman says Freeds’s modus operandi has always been to get potential customers to give the store a first try as it were, knowing that the clothier almost always wins over customers on that first visit.

“Our attitude with our customers and potential customers has always been, ‘hey, give us first kick at the can’ to serve you.’ If we fail, if we don’t provide you with the best all-around shopping experience including quality of our products, our service, and our prices, than shame on us. That’s our fault. If that’s what discounting is, then so be it. But I think our track record shows that we don’t lose customers when they give us a try. It’s the same principles and philosophy that Freeds’ business has been built upon since Sam started eighty years ago.”

Eighty years seems like a lifetime when considering the scope of Freeds impression on the Windsor retail scene, and the greater Windsor-Essex community at large. Babe Ruth was still visiting Detroit three or four times a year, the real “Oscars” were a fledgling idea of Hollywood’s, and a financial crisis of a much deeper and lasting concern were all at play in 1929. Literally thousands of Windsor businesses – small, large and corporate – have come and gone or been swallowed by larger national players. Yet Sam’s little store – the family business that grew and grew and grew, remains as vibrant, robust and strong as ever. Canada’s largest independent clothing retailer indeed!

“We do consider ourselves to be a fashion leader,” says Freed. “We’re extremely proud of what the store and business has become, but you can’t rest on your laurels. Our fathers didn’t do that during the sixties and seventies and Dan and I have tried to keep that philosophy over the past fifteen years. Those simple yet fundamental ‘rules’ passed along by Sam and then our fathers remains as true as ever: Make sure everyone in our family involved with the business gets along, make sure our staff is treated with respect and dignity – because they are the reason Freeds is what it is today - and always remember our customers’ business has to be earned every day. The physical inside of Freeds – like this new department - the kinds of products we offer and how they’re presented, will always be open to change. But those core values; well they’ll always be what Freeds is really about.”