With temperatures on the rise and Memorial Day fast approaching, we decided to have a chat with Ashleigh Stone, the woman behind everyone’s favorite summer accessory: a straw bag from Poolside. No matter the destination, they instantly transport you to sunnier days ahead. “We’re focusing on continuing to create bags that bring happiness to people and feel playful,” she says. That’s an appealing trait—the kind of accessory that doesn’t take itself too seriously.
“I have to say, in general, I always think on the bright side,” says Stone, who is a positive beam of light even while pregnant with her first child in the middle of a pandemic. “When you have these situations that are totally out of your control, I see it as an opportunity to turn inward, do some self-assessment on what makes you happy and look at the things you want out of life.”
For Stone, that meant turning her handbag obsession into a side-hustle turned million-dollar business. “I’ve always been a bag girl,” she admits. “My first job was in finance, and whenever I got my bonus, I’d go straight to Saks and buy a bag. It didn’t have to be the It bag—just something beautiful and unique.” Stone eventually left Wall Street for the world of public relations—and in 2015, she opened up her own store in Montauk called Poolside Collective.
“Usually, I’m wearing a new bag every day. For me, the perfect bag ties everything together—and makes you feel better about yourself during these crazy times.”
Somewhere between balancing her day job in PR and running the store on the weekends, Stone realized a key style was missing from her shop: straw bags. “I couldn’t find anything that was novel or super exciting,” she recalls. “I liked the classic French market tote but thought it would be really funny if they had rap lyrics and pop-culture catchphrases embroidered onto them.”
With this in mind, she set out to design her own. Fast-forward to one year later, Stone made a sartorial splash with Poolside’s debut collection of straw bags, which featured lyrics lifted from Biggie Smalls (“Sip Champagne When We Thirsty”), Beyoncé (“Woke Up Like This”) and Kanye West, only the NSFW kind. “It’s not a bag that I have or will ever carry myself, because I’m not as bold as a lot of people,” admits Stone. “I just had a feeling it would be this zeitgeist-y thing.” She was right on the money: “It was our top-selling-bag, and that’s what put us on the map.”
In one of those quirky twists of fate, stumbled across on Poolside’s Instagram and made a comment that she wanted one. At the time, Stone was on a 10-day trip to Cuba without WiFi. When she returned, every bag on their e-commerce site was sold out and the brand had amassed a flood of new Instagram followers in their wake, all thanks to Kaling.
Stone let customers in on the joke with bags that can be custom-embroidered with their name, initials or an irreverent phrase of their own. “People started getting really creative,” Stone says laughing. “From there, things kind of took off.” The custom bags began landing into the hands of the supremely stylish jet-set. Gigi Hadid took her market tote to the airport, while Gwyneth Paltrow gave out “Bikinis and Martinis” bags as gifts at a bash she hosted in The Hamptons. Guests, like Reese Witherspoon and Molly Sims, loved them so much, Paltrow took a similar route for her bachelorette party in Mexico with personalized bags for her bridesmaids.
Similar to White + Warren, Poolside remains committed to slow fashion. Sustainable and stylish, the bags are woven from naturally biodegradable palm straw and made in small batches by female weavers in India and Morocco, where they are also embroidered and finished by hand. While Poolside has been quietly moving away from verbiage styles (save for custom bags, which are as popular as ever), their latest iteration makes no less of a statement. “I never want to create something that feels basic,” Stone says. “I take a lot of inspiration from vintage bags and reinterpret them within the medium of straw.” See the brand’s newest best-seller: A dotted with over 250 glass crystals that looks straight out of Jane Birkin’s closet. “I always liked her groovy sex-bunny vibe. She’s the biggest straw bag gal of all time.”
Like Birkin, Stone’s bags are essential to her street style, and she test-drives new designs to see what resonates with people: “I’ll wear them out or when I’m running errands. If I get stopped a million times, then I know that bag will do well.” Stone’s approach to fashion is grounded in transformative accessories. “Usually, I’m wearing a new bag every day. For me, the perfect bag ties everything together—and makes you feel better about yourself during these crazy times.”
Since giving birth to a baby girl named Harper, the new mom is keeping things cozy and chic: “Now that the weather is warmer, I’m having fun putting together pieces that are comfortable but still look like an outfit.” In the spirit of feel-good fashion, Stone shared a few of her favorite ways to take the straw bag into summer with White + Warren—just in time for Memorial Day.