How Pickle cracked the code of secondhand fashion practically by accident

Pickle — an app that lets users rent designer-esque clothes, shoes, and purses from other people's closets — has been called the Airbnb of fashion. It stumbled onto its business model almost by accident.

Launched in 2021 as a social-polling app, Pickle let users post polls about potential fashion purchases — from linen dresses to denim jumpsuits — and get others to vote on their favorites. This experiment, dubbed Pickle 1.0, inadvertently built a community of tens of thousands, transforming shopping into a collaborative experience.

“What we noticed in the comments of those polls was a lot of people were recommending things that they already owned,” Pickle CEO and cofounder Brian McMahon told Sherwood News in an interview. “And that's where this light bulb just went off: what if we broke down these barriers and let people rent, lend, and borrow to and from each other?”

After weeks of research and poring over user data, McMahon and fellow cofounder and COO Julia O’Mara relaunched Pickle as a rental app and website in May 2022. Today it features over 100,000 items, 2,000 brands, and tens of thousands of users. Pickle thrives in the realm of “just below” luxury fashion, offering pieces that, on average, fetch retail prices of $400 or more from trendy designers like Rat & Boa, Zimmermann, and House of CB. Since the items are typically available nearby, renters can choose to pick them up in person, pay $8 for a courier to deliver the item, or opt for direct shipping, all through the app.

Pickle joins rivals like Rent the Runway (which many consider the OG of fashion rental) and Urban Outfitters, which rolled out its popular Nuuly rental service in 2019. In 2022, Nuuly topped $130 million in revenue and more than doubled its user base. Unlike RTR and Nuuly, which use their own inventory to rent or sell to users, Pickle gets its supply from consumers' closets — what it calls "microwarehouses.”

Pickle makes money by taking 20% from every transaction, whether it's a rental or purchase. While the business isn't profitable yet, it’s growing quickly. Pickle says it sees thousands of rentals each week, and its total sales value is growing by double digits each month. Investors have taken notice: Pickle secured $8 million in seed funding last October, co-led by investment groups FirstMark Capital and Craft Ventures. Last year Pickle was valued at about $30 million. 

"We believe in marketplaces, and we believe the pure use of the internet is the ability for people to find people," Rick Heitzmann, cofounder and partner at FirstMark, told Sherwood. "And that's where a lot of great business deals have emerged over the years."

FirstMark, which invested in startup superstars like Airbnb, StubHub, and Pinterest, cited Pickle’s strong organic growth as a reason to get on board. It also has impressive retention: 90% of its users are still using the app after a year. Heitzmann said that peer-to-peer models like Pickle, combined with the scale of the internet, offer a way to improve customers' lives while creating value.

“It’s been a really great company so far, and so we continue their view… and you know [they're] delivering a great product,” he said.

Pickle celebrated its second birthday this month and said most rentals were for weddings, birthdays, or a night out. Although Pickle fits are available to ship anywhere in the US, its primary market is New York City, where the company opened its first storefront in December. The lime-green boutique serves as a rental business and warehouse, offering shoppers trendy rentable clothing on racks that they can try on. Since the store’s inventory is also made up by Pickle users, some renters also have the option to stop by the store for an easy pick-up. Meanwhile, the app’s quickly building roots in Los Angeles.

“There are also a ton of different creators and women in the event and entertainment space that need that attire all the time,” O’Mara said. “They have all these different movie premieres or occasions or things that they're going to. Plus, LA has really great weather.”

Social media like Instagram has made outfit repetition more of a stigma, as fashionistas try to avoid wearing something they've already posted on their feeds. Avery DeLacey, a wholesale fashion assistant in New York, hadn't planned to rent out her own clothes on Pickle. But after the app came in handy when she needed last-minute outfits for a summer trip to Portugal, she decided to try it out.

“Obviously New York is expensive and everyone has their side jobs or whatever,” DeLacey told Sherwood. “I've been able to get a good amount of extra cash from renting stuff that is just hanging in my closet that I'm not going to wear anyway right now.”

Pickle's interface resembles popular fashion resale marketplaces like Poshmark and Depop, attracting Gen Z and millennials who want to balance sustainability with staying trendy. While some Pickle users have seen it as a source of passive income, others have turned it into a full-blown operation, earning thousands of dollars a year and making friends along the way.

Hannah, a 30-year-old analyst and self-proclaimed shopaholic, discovered Pickle through TikTok last summer. She decided to rent out her clothes and was one of the first 2,000 users to download the app. Today she has nearly 400 subscribers and 150 rentals.

“I’ve used other rental services like Rent the Runway and Nuuly, but there's no truly on-trend pieces like there are on Pickle,” Hannah told Sherwood. “Because you are really just renting from the girl down the block from you with similar interests and more fashion taste.”

Hannah said she’s already made back the value on one of her Zimmermann dresses, which retails for about $900. Her favorite part hasn’t just been the extra cash but also making connections. She recounted a time someone rented an outfit from her on the app and, after arranging a drop-off time, they discovered they lived in the same building and became friends.

“I have so many funny stories of people I've met through Pickle,” she said. “It's honestly been just so fun. I feel like it makes your city feel smaller too.”

Pickle’s founders say that at some point the app will offer “everything except for houses and cars,” including a men's category. But for now it's about scaling the operation.

“Obviously we’re very focused on locality because the experience of having something dropped off right at your door from someone down the street on the same day is amazing,” McMahon said. “But we do have users popping up in other cities, and we'll be working on expanding to those in the next couple of years.”