Today we’d like to introduce you to Megan Oliver

Hi Megan, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.

I grew up in the Midwest and went to school for apparel design there before moving to NYC, where I interned for Cynthia Rowley and was soon hired as a design assistant. Over the next 15 years, I gained extensive experience in womenswear design, working on everything from ready-to-wear collections to activewear and licensed products like bandaids and accessories. While I had a wealth of design knowledge, I didn’t have much background in childrenswear—except for one baby licensing project early in my career that convinced me I’d never work in kids’ fashion. Funny enough, that changed when I became a mom!

During maternity leave with my first daughter, Penelope (now 7), I struggled to find fun, high-quality kids’ clothing that wasn’t outrageously expensive. At the time, your options were either big-box retailers with subpar quality or designer brands with kids’ lines that came with hefty price tags. I also felt everything had a very baby-cutesy feel and anything gender neutral was only neutrals and pastel yellows and greens. I realized there was a gap in the market and saw an opportunity to create something better. That’s when League of Friends was born—a direct-to-consumer brand offering sustainably-made, high-quality kids’ clothing at more accessible prices. Now, as a mom of two daughters (Penelope and Mabel, 2), I’m proud to have built a brand that families can rely on for fun, thoughtfully designed clothing that will last from one kid to the next, keeping the clothes out of landfills as long as possible.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?

Growing this business has definitely been a bumpy ride. I think most entrepreneurs understand that building a business is tough, but the reality is always more challenging than you expect. As a bootstrapped brand, managing cash flow has been one of the biggest hurdles. There’s a significant upfront investment that you plan for to develop the website, run the first round of production, create packaging, and set up all the necessary tools—and you do all of this without knowing if your efforts will pay off. You’re excited about the launch, but getting your brand in front of the right customers takes more time and effort than you ever imagined. With a product that is as seasonal as clothing, it can be very hard to plan for your next season’s collection without a secure customer base and the sales to back your next production order. I have learned to keep my quantities as small-batch as I can and grow the number of styles and quantities per style as my sales grow.

Another challenge has been the tech side of the business. From managing social media to teaching myself website optimization and testing paid ads, I’ve had to learn everything from scratch and with no prior background in marketing or tech, the learning curve has been steep. But I believe it’s essential to understand these aspects before considering outsourcing them. I want to be informed and able to make educated decisions rather than risk wasting company resources on an agency that may not be the best fit.

Perhaps my biggest struggle has been balancing real life with the demands of the business. When I decided to launch this brand, I also wanted to ensure I could be there for my kids. During the brand’s early days, Covid disruptions were still affecting my eldest daughter’s school schedule, so flexibility was key. I also found out I was pregnant with our second daughter just before launching, which meant planning my maternity leave while being the only employee was quite a challenge. I wanted to give myself time to recover and bond with my baby, but I also didn’t want to put the brand on hold. Juggling being the primary caregiver to my two daughters while my husband works full-time has been tough. But watching my children grow while building this brand has been an incredible experience, giving me valuable insights into the type of leader I want to be when the time comes to hire employees.

With all this said, I have learned so much about myself and the business from every struggle that has come my way and I think it’s making me a smarted and more creative entrepreneur as this brand continues to grow!

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?

League of Friends specializes in high-quality, sustainably made baby and children’s clothing that is colorful and gender-neutral. Our designs are playful, cool, and meant to be enjoyed by all kids, regardless of gender—making them perfect for passing down from sibling to sibling. I’m incredibly proud that our fabrics are made from organic cotton grown in Peru and other natural fibers sourced from humanely and ethically farmed animals in the Andes Mountains.

We partner with a fantastic team in Peru, who spin all their yarns in-house and dye them using natural, plant-based dyes. Their yarns are all made-to-order, which helps us reduce waste by avoiding overproduction.

Our commitment to sustainability extends beyond fabrics and yarns. We’ve worked closely with our production partners to eliminate single-use plastic garment bags, opting for ‘bulk packaging,’ which minimizes waste while still protecting the garments. As a young brand, this is a small step in eliminating single-use plastic bags which has become such a problem in our society, but I hope one day that other larger brands will catch onto this as well. We also ensure that all packaging used to ship our products to customers is made from fully recyclable paper materials, further reducing our environmental footprint.

I’m thrilled to announce the upcoming launch of our trade-in and resale platform in late September. This will allow customers to trade in pre-loved League of Friends clothing for store credits or shop gently used items, keeping our pieces in circulation longer and out of landfills. It’s been a long-time goal of mine, and I’m so proud to see it come to life.

One of the greatest joys of running League of Friends is hearing from our customers. Whether it’s a parent saying their child won’t take off their favorite sweater long enough to wash it, or a grandparent raving about how well our clothing has held up through countless wears—it’s feedback like this that truly drives me. I’m always flattered when people tell me, ‘I wish this came in my size,’ because that’s the level of quality and style I aim for with every piece I create.

Can you talk to us a bit about the role of luck?

I cannot think of any ways luck (good or bad) has played in business, but I definitely believe luck, or rather fate, played a role in me finding love. I lost my cell phone during one of my weeks of college and my (now) husband is the one who found it and returned it to me. From there we had an immediate connection but didn’t end up dating until a few years later. That lost cell phone is the reason I have the great partner and amazing kids and life that I have now.

Contact Info:

• Website: https://leagueoffriends.nyc/
• Instagram: https://www.instagram.com/leagueoffriends_nyc/
• Facebook: https://www.facebook.com/leagueoffriendsnyc

Image Credits

Yumi Matsuo Studio