Monday Swimwear has come a long way from its beginnings as a daily bikini blog. Today, the label operates stores in Beverly Hills and New York, with ambitions that extend well beyond swimwear. For founders Natasha Oakley and Devin Brugman, that growth has been driven by listening closely to customers, focusing relentlessly on fit and resisting the temptation to chase rapid expansion. Here, Oakley talks to Inside Retail about the brand’s entrepreneurial journey, its US retail expansion and the
he philosophy shaping Monday Swimwear’s next chapter.
Inside Retail: Prior to launching Monday Swimwear, can you delve into your career background and how your path led you to becoming a brand founder?
Natasha Oakley: My entrepreneurial journey actually started before the blog, A Bikini A Day, went live. In 2010, I launched a production company, which gave me my first experience building a business and taught me a lot about content creation, branding, marketing and storytelling.
I grew up on the beaches of Sydney, and Devin grew up in Maui, so swimwear had always been a huge part of both of our lives.
In 2012, we founded A Bikini A Day, which started as a simple blog where we shared a different bikini every day. What began as a passion project quickly grew into a global platform and community. Through that experience, we were constantly trying on swimwear from different brands, working closely with the industry and hearing directly from women about what they loved and what they struggled to find when shopping for swimwear.
The more feedback we received, the more we realised that many swimwear brands were not truly accommodating the needs of all women. We were hearing the same frustrations over and over again, whether it was finding enough support for a larger bust, achieving the right fit through the hips, or simply feeling confident and comfortable in a swimsuit.
We became obsessed with solving those problems through thoughtful design, adjustable details and fit-focused development. That insight ultimately led us to launch Monday in 2014, creating swimwear that celebrates and supports women across a wide range of body types without compromising style.
IR: How did you first come up with the concept for Monday Swimwear?
NO: The concept for Monday Swimwear really came from our experience building A Bikini A Day. We were wearing and reviewing swimwear from hundreds of different brands and, through our community, having constant conversations with women about what they loved, what they struggled with and what they wished existed. The more immersed we became in the category, the more we realised there was a significant gap in the market.
At the time, we felt like we couldn’t find suits that were truly comfortable and supportive while still feeling sexy, elevated and timeless. We were also incredibly inspired by the effortless way women in Europe dressed, especially while on vacation. There was such a confidence and ease to their style that really resonated with us, and that became a huge part of our vision for the brand.
From the beginning, we always envisioned Monday as more than just swimwear. Our very first resortwear collections included linen pieces, sarongs and straw accessories because we wanted to create an entire vacation wardrobe. Today, that effortless, elegant and timeless aesthetic remains at the core of everything we do.
IR: How did you decide on the name of the brand?
NO: The name came about while Devin and I were in a taxi in New York City, brainstorming ideas for the brand. We were laughing about how, through A Bikini A Day, we genuinely spent our lives in bikinis seven days a week. At one point, we joked that if you’re wearing a bikini on a Monday, you’re probably having a pretty good day. You’re likely on vacation, by the beach or enjoying some of life’s best moments, and we loved what that represented.
To us, Monday became a feeling rather than a day of the week. It represented confidence, freedom, optimism and that carefree vacation mindset, and it immediately felt like the perfect name for the brand.
IR: What were the toughest challenges you faced in the initial stages of launching and running the brand? What strategies did you incorporate to overcome these issues?
NO: Like most founders, there were countless challenges in the early days. We were learning everything as we went, from product development and manufacturing to logistics, customer service and inventory planning. Building a business while simultaneously learning how to run one can be incredibly challenging.
In the beginning, Devin and I truly lived and breathed the brand, and honestly, we still do. We were running the business from our apartment, packing orders, answering customer emails, developing products and handling every aspect of the company ourselves. There was no separation between work and life, and we were, and still are, involved in every single detail of the business.
One thing that helped us navigate those early years was staying incredibly close to our customers. We listened constantly, adapted quickly and weren’t afraid to make changes when something wasn’t working. We also focused on building the business sustainably rather than growing too quickly, which allowed us to create a strong foundation that continues to support the brand today.
IR: What have been the biggest highlight moments of running the business thus far?
NO: There have been so many special moments over the years, but recently opening our Beverly Hills and SoHo stores has been a major highlight. Physical retail was never something we wanted to rush into. We waited until the timing felt right and until we knew we could create an experience that truly reflected the brand and everything Monday stands for.
One of our mottos is “swimwear that takes you somewhere,” and we wanted that feeling to come through the moment someone walks into one of our stores. We spent years thinking about what a physical space would look and feel like, from the design and materials to the customer experience and product assortment. Every detail was considered so customers would feel transported into the world of Monday.
Even now, I still love spending time in our stores whenever I can. I was recently in New York and stopped by our SoHo store every single day. I love meeting our customers in person, hearing their feedback firsthand and seeing how they interact with the product and the space. We invested so much thought and care into bringing these stores to life, so watching people walk in, find pieces they love and connect with the world we’ve created is incredibly rewarding. It’s a reminder of why we do what we do and how far the brand has come.
For so many years, Monday existed primarily online, so having physical spaces where customers can fully immerse themselves in the brand has been a really special milestone. It’s something we’ve worked toward for a long time, and seeing it come to life has been one of the most fulfilling experiences of my career.
IR: This year, Monday Swimwear opened its second brick-and-mortar store in New York City, after opening a location in Beverly Hills, California. What has the reception been like with consumers thus far, and how has it helped expand the brand beyond its DTC roots?
NO: The response has honestly exceeded our expectations. Both stores have been received incredibly well, and it’s been amazing to see how excited our community is to experience the brand in person.
Our stores allow customers to step into the world of Monday in a way that’s simply not possible online. They can feel the fabrics, try on different fits and immerse themselves in the lifestyle and aesthetic we’ve spent years building. We were incredibly intentional with every aspect of the experience, right down to the lighting in the fitting rooms. When you’re trying on swimwear, feeling comfortable and confident is so important, so we wanted to create an environment that feels welcoming, flattering and luxurious from the moment you walk through the door.
It’s also allowed us to connect with our customers on a much deeper level. We get to hear feedback in real time, help women find their perfect fit and create a more personal experience than we ever could online. While DTC will always be a huge part of our business, the stores have strengthened our relationship with existing customers while also introducing the brand to entirely new audiences who may not have discovered us otherwise.
IR: What other locations may we expect to see Monday Swimwear open physical stores next, and why? What does the timeline for this look like?
NO: Nothing is confirmed just yet, but Miami is definitely a market we love and one that feels very aligned with the brand. In the long term, we’d also love to expand into Europe, where we have a very strong customer base.
For now, we’re focused on continuing to learn from and optimise our existing optimisers, but physical retail remains a big part of our long-term vision.
IR: Aside from physical expansion, what other goals do you hope to achieve with Monday Swimwear over the next year and over the next five years?
NO: Over the next year, we’re focused on continuing to grow the business thoughtfully while expanding our product offering across both existing and new categories. We’re always looking for ways to better serve our customers and continue evolving the brand.
Looking further ahead, we’d love to continue expanding globally, open additional retail locations and further establish Monday as a true affordable luxury brand. Our goal has always been to create a lasting brand that women turn to for every stage of their lives, not just for swimwear.
IR: What is one piece of advice you would give to the day-one version of yourself on your brand founder journey?
NO: One thing I’ve always believed is that if you appreciate the little things, the big things will come. Building a business is a long journey and very much a labour of love. It’s easy to become focused on the next milestone, the next launch or the next goal, but so much of the joy comes from the journey itself.
Looking back, some of my favourite memories are the small wins along the way, like the first customer orders, positive feedback from our community, reaching milestones that felt impossible at the time and seeing years of hard work slowly come to life. I’d remind my younger self to celebrate those moments more often, enjoy the process and trust that progress doesn’t always happen overnight. If you stay passionate, keep showing up every day and focus on doing the little things well, the bigger things have a way of following.
IR: What is your current favourite SKU from the brand?
NO: It’s so hard to choose, but I’d have to say the Clovelly One Piece will always be one of my favourites.
It’s such a timeless piece and one I reach for year after year. As for a newer style, I’m loving the Cannes Top and Bottom. I love the gold hardware details because they make the set feel elevated yet timeless.
Further reading: Monday Swimwear opens Beverly Hills flagship