He’s shaped how Australians dress for 50 years. And he’s far from done

Really though, lunch with Bennett is an opportunity to pick one of the country’s most gifted retail minds – even if it has occasionally ventured into choppy waters, such as the ill-fated expansion of Country Road into the US following the 1987 crash.

Then there was his role in rebooting Georges, the iconic Melbourne boutique department store – an experiment that lasted only 13 months. “[Georges] hurt a lot of people I had great respect for, and who backed me,” he says.

In hindsight, he says he should have taken time off after leaving Country Road, rather than launching head-first into a major project – never mind one as contentious as Georges, about which it seemed every Melburnian, from journalists to shoppers, had an opinion.

“I probably should have taken a year off,” he says. “I was that manic about doing [Georges] … I thought Melbourne needed it. Paris had Collette, New York had Barneys, London had Liberty.”

I point out that of those, two – Collette and Barneys – had closed down. “There’s a lot of ‘was-es’ [in retail],” he laments, as our entrees arrive.

For the first time in our interview, I am nervous. In 2019, after returning from a trip to London, Bennett fell seriously ill with Guillain-Barré syndrome, a neurological disease that’s sometimes known as “locked-in syndrome” due to its impact on the patient’s body. The sickness, which crippled Bennett for 12 months – including four months in the intensive-care unit at The Alfred – has left him with arthritis and joint problems for which he has had several surgeries. “Now, I can’t write, and I used to love drawing and writing,” he says.

Due to his condition, Bennett also struggles to hold a conventional knife and fork. Ever the problem solver, he went online and found a brace that fits over his hand, to which a companion or carer can clip a magnetic fork or spoon. It’s up to me to fit the brace, a task I fumble on the first go, but eventually manage, so Bennett can enjoy his kingfish crudo, while I nibble on the fanciest potato cakes – garnished with whipped cod roe – I have ever tasted.

When I ask what the experience of having Guillain-Barré was like, Bennett pauses to consider his response: “Amazing.” Huh?

Of course, it was difficult, he says, but, “for me, it was all about the ‘now’. I couldn’t deal with the past, I didn’t know what the future was”.

Born in Melbourne, Bennett attended the then all-boys Wesley College, where he developed a passion for rowing, which was first sparked by his sister Jane Parker, who took him to the Head of the River regatta in 1958. He went on to study arts at Monash University, but an academic he was not. “I qualified in rowing boats,” he says.

Bennett says the concept of a crew always stuck with him. “The great thing about rowing is you can’t stop, you can’t lean against the goalposts. You have to have people in the boat who are with you.”

After dropping out of uni, Bennett found his way to Melbourne’s Flinders Lane garment district and Trent Nathan, where he worked as a salesman, but first developed a passion for fabrics. In the early 1970s, hippie culture and tie-dye were on the way out, and “from a clothing point of view, it was quite disorganised”, he says.

Denim was still largely the domain of so-called “workwear” shops, but Bennett could see it shifting into the mainstream. At the same time in America, the Ivy League preppy style was in its early stages. Bennett wanted in. “I always loved ‘weekend’ clothes – you always felt good, they had that ‘lived in’ feeling,” he says, reflecting on Country Road’s early aesthetic and brand DNA.

At first, people tried to dissuade Bennett from making “sportswear” – at the time, the biggest money in fashion was still in dresses. But Bennett could see JAG and Just Jeans were starting to make waves in casual wear. Already, his instinct for retail was spot on.

“I couldn’t say we were a fashion house, we were a lifestyle house,” Bennett says. “There were certain colours we loved and certain colours we wouldn’t touch.”

Like what? For one thing, he wasn’t mad on brights. “We liked to ‘take the top off’ colours, so it was a dusty red, or an olive green,” he says, acknowledging my khaki blazer.

Over mains – a hand-rolled pasta with chicken and hazelnuts for Bennett, and a fritto misto of fish, school prawns and baby octopus for me – I ask Bennett about his (and Country Road’s) role in completely reshaping Australian menswear, including the idea of “split suits”, where the jacket and pants could be worn as separates.

He rebuffs the “revolutionary” tag, but agrees the launch of menswear in 1984 “was a real explosion in the brand”.

“We were showing guys how they could dress without intimidating them,” Bennett says.

As well as his business acumen, Bennett’s design legacy cannot be ignored. His 1984 chambray shirt was re-cut for Country Road’s 50th birthday, and his work features in the permanent collection of Sydney’s Powerhouse Museum. After Georges, Bennett went on to establish a private label for David Jones, S.R. Bennett & Co, which lasted about three years, before he spent a decade as creative director of Driza-Bone.

Still, it will always be the Country Road name with which Bennett is associated, which is why he is saddened by recent allegations against the current management of the company, including sexual harassment and bullying.

The allegations emerge weeks after our meeting, so when I call Bennett about them, he is careful to distinguish between Country Road Group, the corporate entity (controlled by the South African Woolworths Holdings, which includes Witchery, Mimco and Politix), and the brand he founded, as well as its staff.

“There is real leadership and strength in the executives controlling and producing Country Road products … and that will continue [after these allegations are investigated],” he says.

Over the course of his career, Bennett says he has been lucky to meet many of the world’s greatest fashion and retail minds.

“I’ve been fortunate to meet all these wonderful people … [Ralph] Lauren was tricky but funny. We were sitting in New York, talking about Australia. I said to him, ‘When are you [Lauren’s brand] going to come to Australia?’ and he said, ‘I’m not even in f–ing Canada, so you can forget it.’ It was such a New York moment.”

Indeed, Lauren eventually came to Australia. Irrespective of whether Bennett influenced the father of American sportswear, plenty of retail leaders turn to him when they need to solve a problem or expand. His main gig now is at cosmetics and skincare giant Mecca, where he works with founder Jo Horgan on the company’s retail footprint. “I don’t get involved in the ‘goo’,” he says.

“I spend more time telling people what not to do than telling them what to do … all my bad decisions, Georges included, were rushing into things,” he says.

These days, Bennett admires business leaders who meditate and go to bed early over those who work around the clock, as he did at Country Road. He divides his time between the city and his farm at Waratah North, near Wilson’s Promontory, which he shares with his second wife, Michelle (he has two adult daughters with his first wife, Pamela, and five grandchildren).

As much as he loves – and needs – a slower pace of life, you can’t help but feel Bennett, who is sipping an affogato for dessert, still has a fourth, fifth or sixth act to come, at the same time many of his peers are enjoying retirement. But he also has personal goals for this year – to requalify for his driver’s licence and get back on the golf course.

“I’ve still got the buzz,” he says. “How long can you be relevant for? Frank Lloyd Wright had more work at 85 than at 45. The thing you learn as you get older is you start to clarify what things really mean.”

Make the most of your health, relationships, fitness and nutrition with our Live Well newsletter. Get it in your inbox every Monday.