Megan Chiarello is the founder of Leallo, a premium comfort clothing brand headquartered in Sag Harbor. Available in Chiarello’s three stores throughout the Hamptons — SUNNY in Sag Harbor and Gloria Jewel in Bridgehampton and Amagansett — and online, the brand offers chic, high-quality pieces for women.
Chiarello began working in the Hamptons as a waitress at Almond Restaurant in Bridgehampton, where she found an incredible community. She later managed Calypso St. Barth in Southampton, gaining experience in operations, managing staff, and becoming an expert at customer service. She opened her first Gloria Jewel store in 2007 and has since grown her thriving retail business to include Leallo and SUNNY.
We caught up with Chiarello to learn more about her journey.
Tell us a little about your background and what brought you to the East End.
I was born and raised in Shoreham on Long Island, and I’ve always loved everything about the East End — it holds a special place in my heart. Growing up, my family had a place in East Hampton that they would rent out for the summers, so we got to spend winter holidays out here when there were no tenants. After graduating college, I ultimately relocated to the East End since it’s a place that gave me fond memories.
You worked at Almond, where you also met your husband. Tell us about this experience and how it later led to your work in retail.
Yes! I moved out East after graduating college with a degree in Education. Realizing it was not my future, I came out East to my dad’s house to try and figure things out. I was leaning toward a future in the fashion industry in New York City, so I was just out here to save money and network (or so I thought), but I ended up finding an incredible community that I loved so much and an exceptional group of friends at Almond. It was such a fun, authentic group of people that I ended up marrying one of them! I did end up following my plan to work in fashion in NYC, I even considered opening my first boutique there, but the pull was always so strong to come back out East, so my plans changed, as they tend to do for all of us at one point or another.
Tell us about your time managing Calypso St. Barth in Southampton and how this led to the founding of Gloria Jewel.
After spending a few summers at Almond, I eventually took on a more industry-appropriate position working for Christiane Celle at Calypso. I learned so much about the retail industry, the Hamptons community, and myself during my time there. Celle is so incredibly talented and was really a role model for me. Through my time in retail, I truly fell in love with helping women find pieces that made them feel confident and at ease. I especially love working in the Hamptons because so many families are together, and shopping becomes a bonding experience. Multiple generations of women come into the store, genuinely spending quality time as families, bonding over helping each other find special pieces, and feeling good! I 100 percent knew this was my calling. So, in 2007 on a shoestring budget, I opened Gloria Jewel, named it after my two grandmothers, and began my journey.
Talk about the start of Leallo and the opening of SUNNY in Sag Harbor.
I’m thoroughly grateful for the connections and learning experiences I gained from running Gloria Jewel for the past 16 years. Customers really responded well to the feeling in-store and what we were curating. My customer base grew, and we kept opening new locations. I learned what women want to wear while living in the Hamptons and how they like to shop. But I always noticed this market gap; it was hard to find a good white tee shirt that wasn’t see-through and too clingy. At the time, I had a friend living in Peru and working in production with ethical factories, doing wonderful work. It was the perfect opportunity to test out the waters. I created two tees and two tanks, and the response was great. It was so fun to create something you knew your clients needed. From there, I made a lounge set, dresses, jumpers, and now lots of cashmere knits. I ended up opening SUNNY in Sag Harbor primarily because the Leallo line needed its own breathing room outside the context of Gloria Jewel.
Tell us about the fabrics and materials you use for Leallo.
All our cottons are produced in Peru, and we use the finest pima cottons. We strive to make everything with 100 percent cotton. Our knit collection of cottons and cashmere are all made in China. Leallo manufactures in a Fair Trade Certified factory and remains ever-conscious of carbon footprint.
Tell us more about how you’ve been able to scale the brand.
I started Leallo in 2015, and by 2019 I’d gotten so many requests for wholesale that I decided it was time to learn more about this process and hire some sales reps to help me grow that brand of the business. Between 2019 and 2022, we had over 259 specialty stores ordering Leallo regularly, and things proliferated with wholesale and e-commerce. It was exciting how fast it all took off and that people were responding well to the brand, but honestly, it became a little too much for me personally. I was starting to lose focus on what I love, the retail component. I decided to taper down the wholesale business and hire more staff to manage e-commerce as we grow that end of things so that I can be where I love to be, in the local stores, connecting with everyone in person and keeping the new collections and the overall experience tailored to exactly what my customer base needs.
How do you draw inspiration from the East End’s beaches and landscapes?
Everything about Leallo is based on the local Hamptons experience. I wanted to create clothing for the way we live out here. Simple, sustainable, luxe fabrics in classic, wearable styles and color palettes that reflect the world around us. I want women to easily toss on an outfit in the morning that both makes their body and heart feel amazing and also performs exactly how they want it to for the whole day. From school drop-off to the farmstand to walking on the beach to a casual dinner with friends. The landscapes and seascapes inspire the color palettes from Montauk to Westhampton — sand, sky, fields, grasses, driftwood, and gardens. I’m so grateful for what I’ve accomplished with Leallo, and I’m so excited for all the newly branded stores to launch in 2023.
Do you have any favorite pieces for winter and this coming spring?
We’re introducing a beautiful cotton gauze collection this year that I’m so excited about. These dresses are perfect for brunch to beach to cocktails. They are simple, flattering, breezy pieces to toss on for an entire summer day. They’re not too boxy or bohemian, just enough structure to stay pretty, but airy softness for days. They feel good to wear, and like all Leallo pieces, they wash beautifully, season after season, so they’re a simple investment piece.
When you have time off, how do you like to spend it on the East End?
I love the casual lifestyle out here — mostly, you’ll find me hanging out with family and friends, enjoying some casual entertaining at our house in Sag Harbor, hitting the farmers’ markets for all the incredible local produce, and just being in nature as much as possible. These are the places where I find inspiration for my new collections, but more importantly, no matter how challenging life can sometimes be, these are the places and experiences that fill my soul with joy.
I also must wholeheartedly add that I have the most amazing team, many of whom have been with me for many, many years, and there’s no way that I would’ve been able to grow and pursue my passions without them. I truly trust them to take care of our customers and the store, and I am so grateful to have them.
Visit leallo.com.
