AYR’s Maggie Winter: ‘We don’t want to choose between growth and profitability’

Initially, those luxe alternatives only included high-quality denim and other apparel in the womenswear category, but in 2022, AYR expanded into menswear after many requests. Menswear became AYR’s fastest-growing category, seeing three times 2022’s growth in 2023, according to Winter. Because of the new category, in part, AYR has become a $50 million company, growing 5x since 2020.

“[AYR’s] growth has been fast, and looking back, there’s so much [information] we’ve learned along the way tha,t now, we get to use,” Winter said on the latest episode of the Glossy Podcast. “Now that we have an audience, a business, a brand and an audience, I get to be a merchant again and live with great product. [I get to] dream about how to storytell that product … and how to connect with people over it.”

Winter is also thinking about the next phase of the brand’s growth journey. Currently, AYR is 99% DTC and 1% wholesale, with Shopbop being its sole wholesale partner. Along with growing AYR’s digital footprint and community, Winter said she’s working on new ways to provide an experience to consumers.

On the podcast, Winter discusses what’s driving growth at AYR and what’s in store for the brand moving forward. “We don’t want to choose between growth and profitability. We want to generate self-funded growth at a rate that doesn’t exceed our capacity to learn, itirate and guarantee a great experience for customers,” Winter said. Additional highlights from the conversation, below, have been lightly edited for clarity, 

Investing in e-commerce vs. retail stores
“I love retail. I was in New York this winter, and it was so fun to walk around and go into different stores and have an experience and exchange with a person. I think [stores] are a terrific way to get to know a brand, especially a brand that is proud of its product. There’s nothing better than touching and feeling the product and trying it on — it speaks for itself. The thing about stores is that it’s tricky, and it won’t scale as quickly as digital can. [AYR] still has so much growth and opportunity on the digital front and, in a really good week in a store, [we] can make [the same level of sales] in about an hour and a half online. It’s hard to divert investment from that fast-growing channel to another channel that’s probably going to have outside resources required upfront. It’s probably similar in media to the idea of print and digital or print and podcasts, and the idea that it’s a wonderful thing to have, and there are so many benefits, but it is capital intensive, labor intensive and won’t have the same reach that digital media allows us.”

AYR’s customer acquisition strategy
“Catalog is absolutely the most profitable acquisition channel for us. Between 20% and a quarter of the people who receive it are existing customers, and the rest are prospects. That channel has been the biggest unlock for us, and it’s also fun because, in addition to meeting customers, we get to meet some of our heroes. [My friend] Amelia worked with us on our very first catalog. Now, she’s full-time on our team, and she is involved in our brand — she is our brand voice. We like to put little winks in our catalog like, ‘I wonder if anybody will see this.’ We’ve also mentioned people that we love, like New York Magazine art critic Jerry Saltz. We said something in a caption something like, ‘Jerry Saltz liked my tweet,’ We put it on a picture of a girl sitting in front of maybe a gallery, and she had on this awesome outfit: wool trousers and a cashmere sweater. She looked like a cool downtown art scene girl, and he posted it on his Instagram. … In another catalog, something similar happened with Nancy Meyers, who we’re obsessed with. … Catalogs are great for acquiring customers. They’re also great for engaging in pop culture.”

Strategically approaching category expansion
“We love taking a slow approach to [product] development. One of the things I’ve learned is how important it is to live with samples and to live with samples at different stages of development. If it’s not something you’re reaching for over and over and over again, there’s no sense in [producing it]. The world doesn’t need more stuff. Being in a place where we can be independent, set our own goals and our own timeline, and not respond to any external pressure frees us up to be allowed to make things that we find fulfilling and purposeful and that we feel very proud of.”