Flagpole Swimwear

Chances are, the name Flagpole Swimwear doesn’t ring a bell, but if you’re a fan of Solange Knowles (which, duh, of course you are!), you’re well and truly acquainted with their designs. The singer sports the brand’s Lynn swimsuit in that pool scene in the music video for Don’t Touch My Hair and only a few seasons in, the line is backed by the likes of Net-A-Porter and Saks. Oh, and did we mention they’ve just wrapped up designing a swimwear collaboration with Oscar de la Renta set to hit stores this spring too? It’s easy to assume that the line, helmed by best childhood best friends Jaime Barker and Megan Balch is an overnight success, but theirs is a true hustle story.

The pair met and bonded in high school over a shared love of fashion and decided to join forces, trading South Florida in for New York, pledging to start a swimwear label inspired by the dance leotards they grew up wearing. There were years of sharing a bedroom, sleeping in bunk beds and hearing ‘no’ from top department stores before things started to turn around. Armed with a 72-page business plan and a small cash injection from an angel investor, they’ve positioned the brand as the next big luxury American swimwear line for women of this generation.

After chatting with the pair, we realized that while they have their eyes on the prize as far as building their brand is concerned, there’s much more to them than that. They’re fun – a dance session to Bruno Mars’ 24 Karat Magic did take place mid-shoot – and they know what this generation want from a brand and how we want to be spoken to but they are their customers. Here they talk about setting up, learning from mistakes and what to expect from that Oscar de la Renta collab.

Flagpole Swimwear


Megan: We met in our 9th grade science class on a fateful day when our teacher put us in alphabetical order. I was kidding when I mentioned fate, but now that I am thinking about it, it is interesting to think all the way back to our ancestors last names, through all the events that had to go just right, to get us in a class together where our teacher would insist on alphabetical seating. In that way, fate does seem like the right word. We immediately started collaborating on school projects and as we got closer to graduation, the conversation naturally turned to what we would do together in college and beyond. Going into business together wasn’t so much an active choice we made as much as something we knew would eventually happen, like fate. Thank you, Balch and Barker ancestors!


Jaime: I always knew I wanted to be part of fashion in New York. After graduating with a degree in fashion design from the Savannah College of Art and Design, I moved in with Megan in New York into bunk beds and got my first job at a start-up women’s brand. I got to learn through first-hand experience how the fashion district in New York operates. It was during this job that I came upon a factory that makes swimwear, who today does our patterns and some of our production. After about a year, I burned out and decided I needed something a little more stable, so I got a corporate job designing for Macy’s. This was the perfect break for me and what ultimately made me realize that start-up life was more my pace, but that I wanted to work for my own vision. I am not sure how we would have gotten Flagpole to where it is today without my early experience gained in the industry.

Megan: I had zero professional experience in the fashion industry before we started Flagpole, so I think what is important is to have to access to people with experience. Jaime had some experience, but she also had met factories, pattern makers, markers and graders, vendors, production directors, showrooms and PR agencies that we shamelessly reached out to for advice to get started. More so than personal professional experience its crucial to have a clear sense of self (your voice, mission or style, or whatever that means to you), and a nearly unlimited supply of determination.

Flagpole Swimwear
Flagpole Swimwear


Jaime: We both grew up dancing and really wanted our line to be the blend of fashion and function, which at the time was largely overlooked in the luxury market. It’s crazy to think about how much the industry has changed in the (almost) three short years since we entered, but we both feel that our palettes, colour blocking design and high-quality is the value we add to the swimwear market.


Megan: Working at start-ups is the closest thing we had to business classes before we started Flagpole. Jaime worked at a women’s contemporary RTW start-up for almost a year, and I worked at a fashion tech start-up for about 3 months, and one thing struck us both separately throughout our experiences: we would do things differently. I think that gut instinct is important to have, and the willingness to devote hours to researching and not being embarrassed to ask questions, is the other part of it. We recently participated in DENYC, a mini fashion business school hosted through the Fashion Institute of Technology. Getting to talk to industry experts from all different aspects of the fashion industry was a really insightful opportunity to focus on the different parts of our company. At the end of the course, each brand had to turn in a new business plan, which was perfectly timed for us as we are looking to expand into new markets. This program reminded us of the importance of recalibrating and refocusing our strategy so that our approach to business is proactive and not reactive.

Flagpole Swimwear


Jaime: One of the people we decided to approach with our business questions was a family acquaintance who is a successful business owner. He advised us to spend the next month writing a business plan, and said he would read it if we did. We spent the next 30 days held up in our apartment researching, writing, pacing and crying. This was an amazing experience though. It made us sit down and look at each part of our business, including the parts that are not glamorous. As far as what was actually put into the business plan, in so many ways we got away from our plans that we came back close to a lot of them.


Megan: We sought guidance from anyone who would listen, and with our business plan in hand, we landed an angel investor. With our investor, we decided to enter into the designer market of swimwear, which does need to have a certain quality and branding behind it. With that being said, for everything we accomplished, our budget was very much bootstrapped. Jaime and I worked for over a year from our one bedroom apartment, taking on every role from creative director to messenger. We would often show up to bigger companies to pick up and drop off supplies and people would ask us who we were interning for.


Jaime: We always start with selecting the colours (which we are very particular about so sometimes this can take over a month). Then we decide which styles we will repeat, making sure we have a wide arrangement of silhouettes that offer different levels of support and coverage. Then we look at all the feedback from our customers, buyers and press to develop the new pieces that will round out our collection. This is usually the most fun and challenging part of the process that involves tons of sketches, patterns and tweaks. Once we have everything on the table, we start doing line reviews, where certain things get cut, some go back to the drawing table, some are saved for future seasons, until we have a very clear and edited collection.


Megan: Our very first sales meeting ever was at Barneys. We knew someone who knew a personal shopper there, and got them to agree to review our look book. The personal stylist said she liked it and would pass it along to the buying team. We weren’t really sure if she meant it but before we left the store we had an email from the buyers asking when we could meet. The rest of the stores came from many cold emails and being in trade shows. My biggest advice to designers about meetings with buyers is to listen to why some are saying no. Sometimes they are right to say no, and as a designer you should listen, do your research, and adapt, to make it harder for the next person to say no.

Flagpole Swimwear


Jaime: We were introduced to [CEO] Alex [Bolen] by Erika Bearman. The team had always spoken about wanting to do swimwear so it was a really natural process working on this project together. We both have great respect for quality and at the core of both our aesthetics is this love of American glamour. It was interesting to see the Oscar side of that interpretation and our side and where we met in the middle. It was a lot of fun. We got to play with a lot of textures and fabrics that are not necessarily Flagpole and it was amazing. We usually start our collections by figuring out the colour palette we want to use. For this partnership, they already had a colour palette for the collection so we used that as a foundation and did a lot of research on old styles and pulled some inspiration from the ready to wear collection that they were already making and managed to find a Flagpole way to approach the line. It was a lot of very quick back and forth with sketches and tweaks. It all came together in about three weeks. It was right before fashion week and we were both finishing off our collections but it was a great experience. It will be sold with a couple of retailers like Saks and Harrods and will be available both on their website and ours. We’re going to be in a few retailers that we’ve never quite been able to break into before so this is a great way to test new stores. Most people don’t know our name even in the swimwear world, but even people who don’t care about fashion know the name Oscar de la Renta. Just the overwhelming impact and attention being placed on Falgpole by being associated with such an iconic brand is huge for us as a small brand.


Megan: I’m experiencing it right now. I try to be open and honest about it to myself and to the people I work with. It’s hard not to be frustrated about it so I am also trying to remember to be kind to myself about it. I have been making it a priority to do things outside of work, like see movies and go for runs, to give myself perspective. I can feel it working too. Every time I push myself at the gym it makes me realize how good it feels to work hard. And whenever I see something beautiful that others have made, it makes me want to create.


Jaime: We have hit many roadblocks on our journey, and some of them have been really painful. Our team is definitely on the failure-is-not-an-option train. I think giving yourself only a certain allowance of time to be shocked, or sad or angry before you dust yourself off and figure out how you are going to get what you want regardless, is important.