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Power babes, Maggie Winter and Jac Cameron, are redefining the category and staying true to their friendship along the way. We chatted with the pair about building their brand and how empowering each other has been a major key to their success.
What is your hometown?
MG: I grew up in Hershey, Pennsylvania—where the chocolate’s from.

JC: I grew up in the countryside of Scotland not too far from AYR (the seaside town).

What brought you two together? 
MG: We worked together at Madewell in the brand’s early days. I worked in merchandising; Jac worked in design. We bonded over the clothes we wanted to make and over the sorts of wild nights you have in your twenties in New York City. We still bond over the clothes we want to make… but now it’s more like, “Did you see that great documentary on Netflix?”

JC: Maggie and I worked together at Madewell roughly 10 years ago. We knew at that point we just “got” each other. We connected on everything from the styles, to the size of the buys behind them, to the boys we were dating and the experiences we were having as young adults. We knew the partnership we shared was a special one and had our eye on building something meaningful together one day. Maggie is an incredible partner because she shares the exact same passion for clothing—set us free in a vintage shop, and it’ll be hours before we resurface! That shared love and appreciation of quality and construction, craft, and detail brought us together and keeps us inspired everyday.

At what point did you decide to build a business together? What did that process look like?
MG: Our first conversation wasn’t about the brand we wanted to create—it was about the company we wanted to work for. We thought as employees before we thought as entrepreneurs. We talked a lot about who our customer would be: no surprise, she’s a lot like the two of us. And we obsessed over product. That’s our shared passion.

JC: We always knew we would build something together one day. Partnership is important; trust and respect are equally so. Building the business stemmed from this foundation. We had a very clear picture of our brand, our line, and our customer, and we knew we wanted to create a working environment different to the one we were used to in corporate fashion. So we began with that.

What advice could you give on working closely with a friend and balancing a personal and professional relationship? 
MG: We have different and complementary skills, and where we overlap, magic happens. We constantly share what we’re learning with each other; Jac shows me her inspiration and explains her concepts. It’s important for me to understand what informs her vision. Likewise, I share all of the data and analytics about our product and our audience to identify opportunities to improve and grow our business. We have become very good at understanding each other’s point of view. It’s been a huge learning curve for both of us, but we trust and respect each other. Like any relationship, that’s the foundation. Plus, we share a sense of humor. Last Halloween we went to work as Eddie and Patsy from Ab Fab. I have to say, we nailed it.


JC: We had a very strong base as friends and co-workers prior to the launch of AYR, which I feel is a unique point at which to begin. There quickly becomes no delineation between “work” and “life” when your building something with your best friends. We can usually finish each other’s thoughts on almost anything we are working on, and we are very aligned on the brand vision.

What are the biggest challenges of being your own boss and how does your partner-in-crime help you?
MG: The hardest challenge is self-management. There is no one looking down the road ahead of you, no one to tell you when to back off or slow down. It can be difficult to ask for help or to address tough conversations. Fortunately, our founding team consists of four partners with different areas of expertise. I always keep the objective—building the best brand and business—in mind. If it’s the right thing for the brand and the business, I will find a way to make it happen. The four of us share the same goal, although we represent different perspectives. We’re lucky to lean on each other; we have confidence as a collective that would be impossible to replicate as individual leaders.


JC: Maggie and I have two other co-founders, Max and Zandy. We are a very tight team and have each other’s backs. This is great, because there is always one of us at any given time forecasting, predicting, and anticipating the future (the best that we can in a start-up environment). You have to look at the business through a microscope and a telescope at the same time, which can feel disorientating!

How do you divide up the work between the two of you, and how have your roles changed over time?
MG: Our jobs today are so far above and beyond what we’d be doing if we’d taken a more traditional path! Jac designs an entire line, a fully realized vision. Every day we dress head-to-toe in outfits she’s designed stitch by stitch. Denim is still her first love, but it’s amazing to see how she’s translated her talent into other categories. I’ve been able to apply what I learned as a merchant to an entire business, a whole P&L. My favorite part has been the addition of branding—figuring out how to complement Jac’s expertise with humor and emotion. The result is a very authentic blend of everyone on the team.

What about your partner inspires you?
MG: Jac is the best denim designer in the world. She’s way ahead of me, and she’s taught me everything I know about making great jeans. It’s inspiring to work alongside someone with that passion, talent, and experience. She also has a phenomenal work ethic—I would never want to let her down!


JC:  Maggie inspires me daily with her positivity, creativity, and drive. She can give a talk to an auditorium full of people with poise and humor and win over the room. She shoots almost all of our lifestyle imagery herself and has shaped the brand visuals from the inception. She has developed a tone for the brand voice through copy that is relatable, inviting, and emotional. There truly is nothing she can’t do, and it’s an inspiration to work alongside her and have her as my partner in this wild ride.

How do you motivate each other?
MG: We stay very, very connected. We sit a few feet from each other in the studio, and when we’re working remotely, we Facetime. We share what we’re each excited about and worried about and we try to be solution-oriented. Starting a company is not for the faint of heart. It all makes sense looking backward, but looking ahead… there’s always the element of the unknown. We try to build each other up when we need it, and enjoy the ‘champagne moments’ as they happen. There have been a few!

JC: With food, usually. No seriously.

What do you love doing together?
MG: We love shopping together. It’s so important for designers and merchants to experience product together—to bond over the things you fall in love with, to understand each other’s tastes and preferences. We shop together a lot—thrift markets, vintage shops, designer ateliers. We’ve shopped together everywhere from Paris to Marfa, TX. 

JC: Part of the process I love the best is when we get to sit sit down and assort the line with our first samples. This is the first time we see the garments and we joke that it feels a lot like Christmas morning! After doing this for over a decade, that feeling never escapes me. We try everything on and we obsess over fit, details, construction, and fabrication. We go through every piece with this filter, usually with pizza in hand.


What’s the best advice you’ve gotten from the other? 
MG: We like to remind each other, “The world is your oyster!”

JC: “You learn a lot about yourself through other people.” Inexplicably true in every aspect of life.


What is your process when approaching your creative work?
MG: It’s a constant back-and-forth. We try to give each other space, but we’re also super hands-on and invested. We joke that as long as both points of view are represented, it doesn’t matter who’s advocating for a better margin or a more luxurious fabric—we both care about both! Sometimes we switch off.

JC: I’m always absorbing inspiration, whether it be through moving image, film, or photography. I love art and architecture, so those are usually pretty big jumping off points while I begin concepting the line. Maggie and I love a good vintage shop and spend hours obsessing over vintage construction and details. Whether it be a runway piece, French couture, or a 70’s jumpsuit, we both have a deep appreciation for form and craftsmanship.


When do you feel the most empowered?
MG: Creative collaboration gives me the highest high—when we all produce a shoot together, or assort a line, or open a store, or host an event. Seeing everyone operate on such an elevated level with such an inclusive spirit makes my heart burst. Everyone on our team is super different, but we all have two things in common: we hustle and we have a sense of humor. When you’re working at a start-up, those are better than any degree!

JC: We just opened our new shop on Abbot Kinney in Venice. Our team spent one week out there together building, organizing, steaming, painting, hanging art, digging a succulent garden, meeting with press. Those moments are magical, as we resemble a little family chattering away helping each other get the job done. And in the times when Maggie, Max, and I are running around shooting pictures of the work in progress and marveling at the thing we are building, I feel like a proud mom.


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