TIFF fashion advice from two Toronto designers: ‘Go play dress up and have fun’

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Call it siren style: The creations concocted by Toronto's Kirk Pickersgill and Stephen Wong of Greta Constantine are bound to surface on a few red carpets over the coming days. In less than a decade, the two designers, now in their mid-forties, have drummed up an impressive business that now sees their pieces sold around the world.

Pickersgill and Wong met as neighbours in the nineties; Wong worked alongside costume and custom garment whiz Susan Dicks, and eventually Pickersgill moved to Milan to work with Dean and Dan Caten of D-Squared. When the two re-united in 2006, they decided to launch a line of draped jersey fare to entice women looking for easy elegance with a "wow" factor. Though the brand now regularly shows in Paris, Pickersgill and Wong are still loyal to their roots, recently presenting their spring 2016 collection at a pool party at the home of socialite Krystal Koo. I caught up with the pair at their studio to talk about their passion for design, Canadian glamour, and what to keep in mind when dressing for TIFF.

Over the years I've seen so much talent come and go in this country – a real tenacity is required to make it. How do you two inspire each other to keep going?

STEPHEN WONG: This is all we have – we kind of have to go with it. We committed ourselves to this from the start and we've invested so much into it that we have to make it survive. It's also something that we have really enjoyed watching grow.

KIRK PICKERSGILL: Right, it's like that song the Pet Shop Boys did, "Being Boring." I always make reference to that… not being bored. Once we ever get bored of it, I think that's the time to close the doors. As much as it's work, it's entertaining and it's an industry that's so wildly creative that it only inspires us to be creative. Living in Toronto makes you think more, makes you want more, makes you push yourself more to be on that level of the international designers.

Your clientele keeps growing as more and more interesting, stylish women come to you. How much do you rely on that posse who follow your around for inspiration?

PICKERSGILL: If it wasn't for them, we wouldn't be Greta Constantine. We honestly thrive on them. There's so much to enjoy about a woman. Our demographic is so wildly spread, that we can't even tell you what the age group is. It's so diverse and we only learn from them.

WONG: It sounds like a cliché, but you really do have to know your clients and know their needs, know the events that they go to...

PICKERSGILL: …Their personal lives. And we've grown with our client. When we started our client was different. She's 10 years older now. She's had children, she has a new job, she's changed her lifestyle. So we take those elements into what we're designing to bring that forward.

Your kind of glamour is more about a mindset than an age. How has this changed since the early days of the label, or has it?

WONG: Kirk and I come from the age of the supermodels. It is a certain kind of a glamour and there's a certain amped-up drama surrounding it visually. As far as bringing it into this age, it really is something that I don't think is so different because everyone still wants to have that certain initial impact – that "bang" when they enter a room. The wattage hasn't really been turned down. It's just updating and making things more modern.

There really are so few high glam labels to turn to if you want to wear Canadian. How important is it to keep reminding women that Canadian is the way to go?

PICKERSGILL: It's very important. We work a lot with (Canadian actress) Sarah Gadon, for example. We love following her. She, to us, is the epitome of glamour and she's representing Canada. She did the Armani beauty campaign! I think "Wow, who gets that? Who gets that and at such a young age?"

Everybody's buzzing about the red carpet, especially now during TIFF. How driven are you by the idea of your clients stepping out on the red carpet in your clothes?

WONG: It's always a thrill when they do it, but it's not something we've ever courted.

So many do court it though.

WONG: Absolutely. But I think you have to be a bigger machine in order to do it properly. Like we would never, for example, set up a lounge.

I remember being in Cannes in the Dior suite at some ritzy hotel, and there were people running around with dozens of couture creations, really hoping they were going to get at least a couple of them on the backs of the stars. The system doesn't work that way with Canadian designers?

PICKERSGILL: No, it's not just us. I think Canadians on a whole don't really do that. We don't go out and court people. This is more of a relaxed environment. We're so humble. So when you do see someone wearing your pieces, you get that double, triple excitement.

What advice do you have for women who may never have the chance to go to a film premiere but still wants to embrace glamour?

WONG: What I find with a lot of the women that come to us is that they will take the chance and try something on that they wouldn't normally. And I think they're often really surprised at how they look in something. So I think just try new things, try different silhouettes, try different… PICKERSGILL: …Colours! When women come to us, they sometimes have it in their heads that something doesn't look good on them. It's either their arms, or their hips…they're always pointing out the negatives. But we urge them to try something on and see what it looks like. They're usually surprised because our clothing is very forgiving.

Any special tips for gals who are going to step out during the film festival? Should they feel compelled to wear a different dress every night of the week?

PICKERSGILL: I think they have to!

WONG: I would hope that they would try to make an effort.

PICKERSGILL: Or change it up a little. Do something you wouldn't do normally and play. Go play dress up and have fun. Because people are watching, and people are living vicariously through them, so why not?

WONG: How often do you get the chance to get dressed for an internationally recognized event? It's a great opportunity. Run with it! Be excited about the event that you're going to and dress accordingly.

PICKERSGILL: Yeah, and wear comfortable shoes!

Oh, you're such a downer.

WONG: Yeah, I don't know about the comfortable shoes.

This interview has been condensed and edited.