On the factory floor with Montreal farm-to-garment designer Milo & Dexter

Trained as an industrial psychologist studying workplace well-being and intrinsic motivation, Milo & Dexter founder Jobair Jaber realized he was chasing titles and external validation.

"So, I shifted gears, moved back to Montreal, and immersed myself in cultural and creative projects," he says from a cluttered desk in the company's manufacturing space, covered in spools of thread, papers, and product samples.

"Milo & Dexter became an outlet for my creativity and philosophy. I’ve built a company that reflects my values and provides a space for meaningful work."

Working out of Montreal's garment district in Chabanel, Milo & Dexter today has become somewhat of a multihyphenate company—a retailer, a manufacturer, a lifestyle brand, a cultural collaborator, a content creator—that's since made a name for itself through garments.

It's a new face in an old trade: Sourcing wool directly from Canadian farms that's processed through cooperatives and sent to mills both big—like New Brunswick's Briggs & Little which date back to 1916—and small with artisanal mini-mills for small-batch processing, Milo & Dexter is creating specific products with traceable origins.

"For us, it’s about creating timeless products. We draw inspiration from Canada’s history, like the wool mills in Quebec’s Eastern Townships, which were among the oldest in the country."

Spinning threads

Starting five years ago as what Jobair calls 'a concept brand', early days were spent producing locally in the city, something that necessitated evolving into a manufacturer.

"We invested in space and machinery, and gained experience by making products for hotels, restaurants, and other businesses. Unlike many manufacturers who specialize, we had to be flexible due to local demand and tight timelines," he explains.

During that time, Milo & Dexter re-evaluated what its house label should represent, and decided to focus on creating a brand rooted in Canadian values, showcasing materials sourced locally.

Now, the company primarily works with Canadian wool, building a farm-to-garment model: "We collaborate directly with farms, process wool in Canada, and turn it into garments—everything from sweaters to blazers. This focus is still developmental because the infrastructure for wool in Canada largely collapsed in the 1970s. Reviving it has involved a lot of R&D and advocacy," Jobair explains.

About 75% of the business is manufacturing—both for their brand and other clients—with a made-to-order retail approach. They produce two main seasons each year, allowing them to avoid overproduction and maintain strong relationships with independent retailers and larger partners.

"We’re redefining what 'Canadian' clothing can mean in a multicultural and evolving society."

Dyed in the wool

"Wool is a significant part of our identity, especially as we’ve developed expertise in it, but it’s not our only focus. We still produce garments using materials like Merino wool and cotton, often sourced internationally," says Jobair.

"Canadian wool, though, is becoming central to what we do, particularly as we explore blending it with softer wools from other regions."

Beyond wool, Milo & Dexter also manufactures for other brands to sustain them. They’ve worked with companies like Sheertex, hospitality groups like Fogo Island Inn, and local cafés. These collaborations help keep the light on while allowing them to explore innovative projects like Campaign for Wool Canada.

Joining organizations like the Canadian Wool Council and initiatives supporting the wool industry, Jobair's daily work has come to include as many operations as it does raising awareness about the origins of materials and the value of local production.

"When people think about where their clothes are made, they often focus on design or stitching. But the material itself—the largest component of any garment—is frequently overlooked," he says.

"For us, it’s about creating timeless products. We draw inspiration from Canada’s history, like the wool mills in Quebec’s Eastern Townships, which were among the oldest in the country. These mills are now mostly museums, but they embody a craftsmanship we’re working to bring back. At the same time, we’re redefining what 'Canadian' clothing can mean in a multicultural and evolving society."

Preserving the old ways

Montreal has a unique place in North America as one of the last remaining hubs for garment manufacturing.

Historically, it was a powerhouse, especially in suit manufacturing, and the city was the largest producer of suits in North America up until the 1980s. Since then, Jobair says, free trade agreements went into effect and many companies shifted production offshore to reduce costs, leading to the decline of local mills and factories.

"What remains today is a more niche industry. Montreal still has a district dedicated to garment manufacturing, though it’s being rebranded as District Central to attract more tech and real estate development," he says.

"We’re at a crossroads. Many business owners in the garment sector are in their 50s or older, and there’s a lack of younger entrepreneurs entering the field. If we want to keep this industry alive in Canada, consumers, businesses, and governments need to value local production more."

That comes with tension: The city wants to preserve its manufacturing roots, but high rents and urban redevelopment make it challenging for small manufacturers like us to survive.

"Despite these challenges, Montreal is still a leader in garment manufacturing in North America. It’s comparable to Los Angeles in terms of its infrastructure and capabilities. Other Canadian cities like Toronto and Vancouver don’t have the same ecosystem. Here, we have a concentration of skilled workers, machinery, and a culture that supports the industry," says Jobair.

"But we’re at a crossroads. Many business owners in the garment sector are in their 50s or older, and there’s a lack of younger entrepreneurs entering the field. If we want to keep this industry alive in Canada, consumers, businesses, and governments need to value local production more."

"When people think about where their clothes are made, they often focus on design or stitching. But the material itself—the largest component of any garment—is frequently overlooked."

A new face of an old trade

While scaling Milo & Dexter's operations remains challenging due to outdated machinery and broken supply chains, Jobair is focused on working with government programs to modernize the company's infrastructure and make processes more cost-effective.

"My vision is to create a brand that embodies timelessness and connection to nature. I’d like to move our factory closer to the countryside, near the farms we work with, creating a 'wool belt' ecosystem similar to those in England. This would deepen our connection to the materials and foster sustainable practices," he says.

"Long-term, I want Milo & Dexter to become a generational staple—a brand known for quality and integrity, like Harris Tweed or Burberry. We’re investing heavily in R&D, exploring ways to enhance Canadian wool by blending it with softer materials. While some of our products are still in the experimental phase, we’re steadily closing the gap between concept and execution."

As the company changes and adapts to the present, every day brings something new to the factory floor—whether it’s collaborating with farmers, tackling production challenges, or innovating with materials.

"It’s a privilege to be this connected to the process and the people involved."