Chris Dobbs started selling shirts made in a garage in Marton 26 years ago and transformed his made-to-measure menswear into the Working Style brand which now dresses some of the biggest names in the country. He says there are more men buying $10,000 suits in New Zealand than you might expect.

1. Can you name three items of clothing that you would never be seen wearing?

A casual singlet - I'm not a singlet kind of guy. Too skinny and scrawny. Budgie smugglers - I wear square-leg trunks when swimming, I'm from Marton. And a night shirt. What do I wear to bed? A sensible T-shirt and boxers.

2. What's your best door-to-door selling story?

Being broke - I mean really skint - I went selling at one of the big ad agencies in Auckland. I came out with my fabric swatches and orders in one pocket and $3000 dollars cash in the other. It was the 1980s! But then I realised I would have to make 20 shirts in a week which was an impossible task at the time. I'd decided straight out of Massey University that I wanted to do my own thing but the first 18 months of door-to-door selling was shocking. People were nasty to you and you had to slip into buildings, there was no base to work from and it was bad for your self esteem. It was a tough way to learn about business, but you really learned.

3. You had a mentor - who is now 80 years old. Do you still work with him?

Yes, John Marchant who I was introduced to by a friend of my father's. He's ex-military and uses military style of planning. It's not that fluffy stuff you get in a lot of tertiary models - it's "What's the situation? So what? Who will do what by when?" We use him as a planning mentor when writing strategic and operational plans and it's kept us out of the s*** for 26 years. There's probably someone younger and brighter and full of beans who could add a bit, but fundamental business advice transcends the generations, so age is irrelevant. In our game longevity is everything.

4. Aren't the Playboy Bunny pictures in your dressing rooms a bit sexist?

In 20 years we haven't had a complaint and I think a men's changing room is somewhere you can get away with it. It's a vintage montage and discretely positioned behind a closed door.

5. Could the average punter tell the difference between a $1000 suit and a $10,000 suit?

It's like the difference between a $200,000 car and a $40,000 car - it's the luxury of the experience and the delight in the nuances of that luxury experience. Someone who's starting out in the workforce needs a nice, well-fitting suit but the CEO of the company they're working for, who has been at the coalface for 40 years, wants to look and feel a bit different. A lot of it is in the fabrication which we bring in especially from England or France. There's goat's fibre and cashmere, then the embellishments and finishing will fit that fabrication.

6. How many Kiwis can shell out that sort of money?

More than you think. There is an increasing demand for luxury items in New Zealand. With globalisation, the Kiwi is evolving into a far more sophisticated bird. Expats returning, new migrants arriving and home-grown success creates plenty of opportunity.

7. Your brother Tim is also in the business. What are the perils of that?

It is not a perilous dynamic; I am the eldest so Tim just does what he is told. Not really - we just get on very well. If I'm mean to him, my father will ring and tell me off.

8. Who is better dressed - you or your wife Penny?

Penny. She's incredibly stylish and a perfectionist. I don't think we have the same aesthetic necessarily. We're quite different, with individual tastes and preferences and, obviously, I kowtow to hers. I've learned in 18 years of marriage you don't hang pictures without head office approval.

9. How has having children changed your perspective?

I have three children - Imogen is 16 and has Down syndrome, Ted is 12 and Amelia, 9. Fatherhood puts a different slant on things and having a special-needs child puts another one again because you have an immediate sensitivity or protectiveness for people who are vulnerable and need a hand in life. The biggest and brightest star in our family is Imogen but the worst day you and I have is nowhere near like the one she may have. She's such a cool kid - positive and energetic and she can be a nightmare too. But she's the glue that binds our family together.

10. Medical technology may mean that Down syndrome children do not exist one day. How do you feel about that?

I believe in people's right to do what they have to do for themselves and their families. I'm not black and white about it but I equally cherish who and what Imogen is.

11. Are Kiwi men afraid to express themselves through their clothes?

I think the mindset has changed considerably over 26 years. There was a time when New Zealand men were poorly dressed but now the sophistication has really come up to a level where you can express yourself with a flourish or a quirk or detail. Provincial New Zealand is a hell of a lot more sophisticated too. I was in Te Awamutu the other day and while the look is more agricultural, and you're always going to have gumboots lined up outside the accountant's office, the young guys really know how to dress when they go to town.

12. What's the best business advice you have ever been given?

Turnover for vanity. Profit for sanity.

By Sarah Stuart Email Sarah