In Conversation With

Shannon Carleton, Founder & Captain at Yacht Kelpie

Kelpie has 97 years of history, and to even begin to tell her story would be a whole chapter on its own. But I will say she’s her own little universe. It’s like she has a soul, and you feel her presence the moment you step aboard. And when you combine that with the crew’s energy, it creates something truly special; an atmosphere that’s intoxicating, alive, and unlike anything else.

The Hamptons are magical on their own- there’s a reason everyone flocks here in the summer. But sailing here is another layer altogether. The shoreline may be buzzing, but out on the water it feels like a parallel universe; more serene, more exclusive- almost like it runs on invitation-only. It’s the same Hamptons playground, just elevated- with its own rhythm and world.

How has sailing influenced your approach to style? Is there a particular silhouette or fabrication you gravitate towards?

Sailing has shaped my style in two ways. First, I have to be practical: I spend my days in the wind and sun, often in cooler spring and fall temperatures, moving sails and working winches from the helm. My clothes need to let me move freely and adapt to the elements. Living aboard Kelpie adds another layer; there’s no ironing or dry cleaning at sea, and sometimes I’ll go weeks without stepping on land. I need pieces that always look good and are easy to maintain. 

Donnie Boxy V-Neck Tee & Dune Crop Pant

The best moments are when I’ve been actively sailing- sheeting in the main, steering through a tack- while guests are gathered at the cockpit table. I love that my clothes allow me to move freely for the work of sailing, yet still feel feminine and polished as I’m hosting at the same time. That’s when comfort and elegance truly meet life on the water. 

If you had to sum up your sailing style in three words, what would they be?

Elegant, practical, ladylike. 

Princeton V-Neck Sweater & Dune Crop Pant

The ‘I-just-threw-this-on’ Hamptons aesthetic is in. What’s your style advice for women who want to channel that laidback look?

Confidence is everything. The Hamptons look isn’t about perfectly put together- it’s about owning what you wear. If you feel good in it, you set the tone, and others pick up on that energy. Whether it's linen, a sundress, or something simple you pulled from your closet, wearing it with pride instantly makes it chic. The right pieces feel effortless when you wear them with pride, and that’s what makes the look timeless. 

What’s your “can’t live without” piece of clothing on the boat? 

The Ellie Sleeveless Dress in white is my absolute go-to. I wear white every day, and this dress strikes the perfect balance; it’s long enough to feel elegant, but with that just-right tea length that still keeps it practical. The fabric has enough structure that I don’t have to worry about the wind, and the pockets are essential for my sunglasses, which are constantly on and off throughout the day. I also love the collar, because it layers beautifully under my other stable, the Maidstone Cable V-Neck cashmere sweater. As the sun sets, I usually have the sweater draped around my shoulders or right beside me at the helm. The neutral tone goes with everything, and the cable knit gives a subtle nod to classic maritime style.

What season do you love dressing for the most Out East?

Fall, more specifically, September. It feels like the best of both worlds. The days are still warm enough for sundresses and that sun-kissed glow of summer, but the evenings bring just enough chill to reach for a favorite sweater. I love that in-between balance, when layering becomes part of the look; draping a sweater over a dress feels effortless yet intentional. 

Lastly…you don’t have to give away your best kept secrets, but what’s one of your favorite spots in the Hamptons to sail to?

The Pridwin on Shelter Island is a favorite. The sail there is just long enough to feel like a journey, and I love that they have moorings for Kelpie so we can tie up, hop in the tender, and head in for lunch. The whole place has this vintage summer vibe- it’s one of my favorite spots on the island.

Dune Solid Crewneck & Dune Crop Pant

Photographed by KCollections.