Nick Wooster knows clothes. More importantly, he knows how to wear them.
The international street-style fixture has spent decades working across fashion and retail, but it’s the way he puts clothes together that has made him one of menswear’s most photographed and imitated figures. His signature mix of traditional tailoring, workwear, military references and the occasional wild card has long made the case that dressing well doesn’t have to mean dressing predictably.
When Complex Canada sat down with Wooster at Modern Ambition’s new flagship at 101 Yorkville Avenue in Toronto, ahead of the store’s evening launch celebration, he demonstrated the point in typically Wooster fashion: a pair of oversized fatigue pants from cult Japanese label Needles paired with a jacket he had pulled right off the rack of the Yorkville store.
“I think what’s interesting is to have one thing that’s classic and one thing that’s just a little bit off,” Wooster says. “That’s the trend I’m most interested in right now: one thing classic and one thing off.”
It also happens to be a pretty good introduction to Modern Ambition itself.
The Winnipeg-born menswear label deals largely in the familiar building blocks of a grown-up wardrobe—tailored jackets, suits, crisp shirts, cashmere polos and quarter-zips, and technical outerwear—but approaches them with the understanding that the rules around how men dress have changed. Jackets are softer, tailoring is easier and pieces that might once have been confined to the office are designed to work just as easily with jeans, sneakers or a T-shirt.
Now, after launching just last year, Modern Ambition is taking that idea across Canada. The brand opened its first boutique at Winnipeg’s True North Square before arriving in Toronto’s Yorkville neighbourhood in July earlier this year. Calgary followed on October 8 with a location at The CORE, while a Vancouver boutique at 918 Robson Street is set to follow in November.
But while Modern Ambition may be a new name, there’s some serious Canadian fashion history behind it. If you grew up in Canada in the late ’80s or ’90s, there’s a decent chance you—or at least someone in your class—owned a Mondetta sweatshirt. Founded in Winnipeg in 1986, Mondetta became a Canadian fashion phenomenon, its flag-emblazoned sweatshirts and sportswear seemingly everywhere for a time. Even its name reflected the global outlook behind the brand: Mondetta essentially translates to “small world.”
Nearly four decades later, the people behind Mondetta have opened up a decidedly more grown-up chapter. Modern Ambition was co-founded by CEO Ash Modha alongside parent company Mondetta Clothing Inc., applying decades of apparel experience to a very different menswear landscape.
“The vision for this collection was to create clothing that feels timeless, yet completely attuned to the demands of modern life,” Modha said when Modern Ambition launched in 2025. “It’s about dressing with quiet confidence—no excess, no compromise—just enduring style and purpose.”
That “quiet confidence” is easy enough to see in the clothes. There are no giant logos or obvious attempts to chase hype. Instead, Modern Ambition concentrates on pieces meant to do some heavy lifting in a wardrobe: softly constructed tailoring and Italian fabrics for the knitwear, shirts, and outerwear, often with technical details incorporated without making the clothes look technical.
For Wooster, though, part of the appeal is considerably simpler. “I think that what they’re doing is serving a part of the market that is completely underserved,” he says. “They have great value, great style and great taste for not an offensive price.”
It’s a very Wooster way of putting it, but the point lands particularly well in 2026, when shopping for menswear can sometimes feel like choosing between a $40 fast-fashion shirt and a designer jacket with a four-figure price tag. The middle—where good fabric, construction and style meet a price that doesn’t require a minor financial intervention—can be surprisingly difficult to navigate.
That gap is where Modern Ambition starts to make sense. Its current suits run from just under $1,000 to around $1,300, while jackets, knitwear and shirts occupy a space that feels elevated without wandering into stratospheric designer pricing.
“It’s easy to find very expensive clothes. And it’s easy to find very cheap clothes,” Wooster says. “But it’s hard to find something in between that doesn’t scare you when you look at the price tag, but at the same time you know that there’s quality there and there’s something that you can build a wardrobe on. I think that’s really interesting.”
And “middle ground” doesn’t have to mean boring. Wooster points to a double-breasted herringbone suit as one of his favourite pieces in the current collection, along with the jacket he was wearing when we sat down to chat that afternoon. He also singles out the knitwear—a cashmere polo, quarter-zip and cardigan—as pieces that caught his eye.
Those choices say quite a bit about where menswear is right now. Tailoring is back, but not necessarily in the way your father wore it. Pants have become wider, proportions looser and suits less precious. A double-breasted jacket can work with a knit polo; a cashmere cardigan can be worn with fatigues rather than pressed trousers.
Modern Ambition calls its approach “Technically Tailored,” but the idea is fairly simple: take the things men have always worn and make them work better for the way men dress now.
Wooster’s own outfit that afternoon essentially provided the styling lesson. His Modern Ambition jacket was the polished part; his Needles fatigues threw the whole thing slightly off balance. Neither piece was particularly radical on its own, but together, they felt modern.
That’s also why it’s becoming increasingly difficult to define what exactly makes Canadian menswear “Canadian.” A guy in Toronto can follow what’s happening in Tokyo, Copenhagen, London or New York from his phone, buy many of the same labels and absorb the same silhouettes at essentially the same time.
“I think especially now, you can be anywhere in the world and have access to the same information and clothes that someone in another country has,” Wooster says. “Those ways of being distinct are not as clear as they once were.”
What he does notice here is a willingness to experiment.
“I see an adventuresomeness in the way men here in Canada want to dress,” he says. “I feel like Canadian men are very plugged in and they know what’s going on.”
Modern Ambition is betting on exactly those guys. Opening stores in Winnipeg, Toronto, Calgary and Vancouver within a relatively short window is an ambitious move for a young Canadian menswear label, particularly when so much fashion shopping happens through a screen. But the clothes themselves make a case for getting back into a fitting room. Fabric matters. Fit matters. Proportion matters. And, sometimes, figuring out whether you can pull off that double-breasted herringbone suit requires doing more than adding it to an online cart.
Which brings us back to Wooster’s deceptively simple rule for getting dressed. The interesting part isn’t necessarily owning the loudest or most expensive thing in the room. It’s what happens when something familiar gets pushed slightly out of place: wear the tailored jacket with oversized fatigues. Put the polo under the double-breasted suit. Throw sneakers underneath trousers that once would have demanded polished Oxfords.
One thing classic. One thing a little bit off.
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