EPISODE 03
In this episode of The Business of Modelling, Tessa Dewing visits Milk Management’s London HQ to sit down with its founder and managing director, Anna Shillinglaw. From her own modelling career in the 90s to building one of the UK’s most inclusive and influential agencies, Anna shares a refreshingly honest look at what it takes to thrive in the fashion world.
She talks about working as a model during the height of the heroin-chic era, the challenges of transitioning to curve modelling, and why she eventually walked away from the camera. Anna opens up about launching Milk from her spare room, pushing for better representation, and the ongoing fight for diversity. Now overseeing the Milk Collective – spanning fashion, digital, and broadcast, Anna reflects on building an empire with heart, humour and fierce determination.
This episode is a must-listen for anyone navigating fashion’s changing landscape or dreaming of shaking it up from the inside.
Anna Shillinglaw on Building an Empire, Championing Curve Models and Why Fashion Still Has Work to Do
Interview by Tessa Dewing for The Business of Modelling podcast
Anna Shillinglaw is a force in the modelling world. Founder and managing director of Milk Collective, she has spent over two decades reshaping the industry -from curve model to agency leader, mother, and unapologetic advocate for change.
I met Anna at Milk’s buzzing London office to record our episode of The Business of Modelling. Over the course of our conversation, she shared her journey from being scouted as a teenager to running one of the UK’s most progressive talent collectives.
“I Was Always a Dreamer”
Anna’s upbringing was anything but ordinary. Raised between Kuwait, Saudi Arabia and Hong Kong, she attended nine different schools before being scouted as a teenager. By 17, she had left her A-levels behind and moved to London with £200 and a dream.
Her career took off quickly, booking jobs with Vogue, Elle, and lingerie campaigns that earned her steady income. But fitting into the industry’s standards wasn’t easy. “I had boobs and a bum, and that just wasn’t the aesthetic back then,” she said. “They wanted me to be this boyish waif, and I was the girliest girl you could imagine.”
The Curve Conundrum
Eventually, Anna transitioned into curve modelling, but even that came with confusing contradictions. “At a UK size 10 or 12, I was too big for straight-size modelling and too small for plus-size. So I was told to gain weight – or pad myself.”
She describes the absurdity of padding with drag queen-style inserts to fit client expectations and the mental toll it took. “One day I was too small. The next I was too big. And I just thought, ‘I’m done.’”
From Model to Founder
When she became a mother, Anna decided it was time for a new chapter. “I didn’t want to rely on anyone else financially. I’d worked hard for too long.” With a few model friends and a homemade website, she launched Milk from her spare bedroom in Surrey.
Her mission was clear: to represent models of all sizes and backgrounds and to challenge outdated beauty standards. “At the start, people dismissed me. They called it a plus-size agency like it was a dirty word. But I kept going. I knew we were on the right path.”
Diversifying the Industry
In 2015, she expanded with Milk Digital, recognising the growing power of influencers. And in 2023, she rebranded to Milk Collective, adding Milk Broadcast to support models moving into TV, presenting, and beyond.
“I didn’t want us to be pigeonholed as just a model agency. We’re about full-spectrum talent and longevity. This industry needs to make space for people at every stage of their journey.”
Creating a New Standard
Today, Milk is known for its inclusive approach – championing everyone from high fashion curve models to content creators and TV personalities. But Anna admits that progress is still slow. “At Milan Fashion Week, only 10 designers used curve models. It’s outrageous. We still have so much work to do.”
She credits Milk’s success to tenacity, creativity, and her unwavering belief in doing things the right way. “I’m proud that I’ve built something strong and kind. I don’t want to run a toxic office. I want people to feel supported, seen, and excited to be here.”
Advice for Aspiring Founders and Bookers
Anna is clear that running an agency isn’t for the faint-hearted. “You have to be ready to fail, to get back up, and to work around the clock. But it’s worth it. It’s the best job in the world.”
And when it comes to scouting models? “It’s instinct. It’s that unteachable spark – someone who walks into the room and just has it.”
Anna’s journey is a testament to grit, vision, and challenging the status quo. She built her business with no blueprint, just a clear sense of purpose. And the industry is better for it.
We’re so proud to share her story.