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Maggie Winter, Co-Founder & CEO

Maggie Winter

Co-Founder & CEO, AYR

Maggie Winter grew up in Hershey, Pennsylvania, and got an informal start in retail as an undergrad at the University of Michigan, where she made and sold graphic tees at a boutique on campus. Those tees would soon accompany her to her first job interview with Mickey Drexler at J.Crew.  ‘I had the incredible fortune to learn from the greatest merchant in the world,’ Winter says of her eight years under Mickey’s leadership.  As a merchant at J.Crew, Winter led new channel and new brand growth, as well as turnaround businesses throughout the company.

Three years ago, Maggie Winter and Jac Cameron, former colleagues from J.Crew & Madewell, imagined the brand they wished existed. 

Their vision came to life when Winter met Andy Dunn, co-founder and CEO of Bonobos.  Dunn wanted to leverage the successful infrastructure of Bonobos into womenswear, and saw the potential entrepreneur in Maggie to lead the charge.  Incubated by Bonobos, AYR launched its debut collection in February 2014, offering a full range of women’s denim and contemporary essentials, available at AYR.com, Nordstrom, Shopbop and Goop.  ‘Andy taught me that nothing is impossible,’ Winter says.  ‘He’s a true visionary and believer in digitally native brands.’ 

‘The retail landscape is evolving quickly. AYR, which stands for All Year Round, is all about slow fashion fast,’ Winter says.  She and her co-founders see a powerful new consumer in the market – a busy, purposeful woman who lives her life digitally.  ‘We identify intuitively with our customer, her life is complicated, but her clothing shouldn’t be.  We want to simplify everything, in product and process’ Winter explains.

AYR has seen triple-digit growth in its second year, winning accolades from press and retailers alike since launch (Vogue described AYR’s jeans as ‘a gift from the denim gods’ and Nordstrom began carrying the line in top markets, doubling door count in their first year).  AYR is currently in the process of spinning out from Bonobos to fund rapid growth.