Designer To Watch: Poolside Founder Ashleigh Stone

It’s easy to see why Gwyneth Palthrow would be a fan.

Launched in 2016 by Ashleigh Hults during a winter trip to St. Barths, Poolside quickly went viral with their eye-catching, hand-embroidered straw bags. Inspired by French market totes and embellished with cheeky pop culture references, you can now also custom order your very own, picking size, phrase/word and color.

Since bursting onto the scene, the brand has also expanded into many other shapes and styles, creating bags regularly worn by the likes of Gwyneth Palthrow, Priyanka Chopra, Reese Witherspoon, Molly Sims, Romee Strijd, Emily Ratajkowski and other fashionable women around the globe. The brand’s DNA, however, remains irreverent, luxe beach vibe.

We chatted with founder Ashleigh Hults to find out more about Poolside, her background and what’s to come.

The Fashion Spot: Can you tell us a little bit about your background before starting Poolside?

Ashleigh Stone: I grew up in my grandmother’s sewing room and always found my greatest joy in designing and making things – sewing, crocheting, embroidery. Professionally, I started my career in finance, working at investment banks. Then, I pivoted and worked in luxury fashion and wellness PR for about 4 years before launching Poolside.

tFS: How did Poolside come about?

AS: In 2016, I opened a boutique in Montauk which was situated poolside at a boutique hotel. I stocked many emerging brands from young designers, but couldn’t find any straw bags that I liked. I loved the classic market baskets that I saw in France, but I thought it would be fun to let people customize the bags with knick names or cheeky sayings. At that point, Instagram was just taking off and I knew that the bags would go viral as people started to share their custom bags.

tFS: Is what you had in mind when launching the brand what it is today?

AS: When I launched the brand, I had no business plan or expectations. It was very much a side hustle. Sometimes, I wish I was more prepared for the virality of our launch moment, but I have learned so much along the way and I’m excited about how we’ve evolved as a brand.

Designer To Watch: Poolside Founder Ashleigh Stone

tFS: You’ve been on so many celebrities – how did that come about?

AS: All of our celebrity endorsements are completely organic — they have all reached out to us through Instagram or email, or they were gifted by one of their friends! Some of them have even ordered directly on my website!

tFS: Was there ever a point you thought about giving up and if so what made you stick it out?

AS: I want to be super honest with this answer because I find that there are so many fluffy responses out there when it comes to business interviews and I want to be real and relate to others that are working so hard to grow their businesses. My business is completely bootstrapped and my team is small. It’s hard work and I have never taken a paycheck from the business. There have been so many times that I feel like giving up, but then I remind myself that building slowly and on my own terms is a privilege. I also like to think through some of the pain points, and how I can fix them. For example, I will look at the business from a very high level standpoint and say “We’re doing so well now. However, XYZ is a big operational problem and, if we fix it, I know we can double our business with this major retailer.” Then, I put the plan in place and march towards my goals. I also always remind myself to be “fearless” because life is short so that I feel more comfortable taking calculated risks.

Designer To Watch: Poolside Founder Ashleigh Stone

tFS: How do you deal with other brands knocking you off?

AS: From the start, I decided that I wouldn’t care at all. I could either spend my time getting upset, or I could come up with new designs and ideas to further expand our business. I decided that the later mentality would be more productive. I don’t own embroidered straw beach totes — they have existed for years. However, we do offer quality control, speed, and a lifetime guarantee. We have an atelier in Brooklyn, so if someone needs a repair on their bag, we do our best to fix it for them. We want to be a good partner to our customers, and to create items that people can enjoy for life.

Designer To Watch: Poolside Founder Ashleigh Stone
Ashleigh Stone

tFS: What are some of the biggest anxieties when it comes to running your own business?

AS: I find production and customer service to be the most anxiety inducing aspects of the business. So much so that I’ve invested in professionals to help me in these areas! 

Designer To Watch: Poolside Founder Ashleigh Stone

tFS: Anything you can tease for 2023? 

AS: We are still planning 2023, but we do have one exciting collaboration in the works! We’re also working on re-launch of our website with a mini rebrand to showcase our evolution and the brand we are today. We are also excited to launch new categories, such as travel accessories and RTW.

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