Set Sail With Sailormade

Hardware and jewelry are pretty unusual bedfellows. But Sailormade, a new accessories brand that creates nautically inspired pieces from real sailing equipment, has ingeniously combined the two to create a one-of-a-kind collection for sailors and landlubbers alike. Founded in 2011 by James Ashton and Carla Sinatra, the company continues to expand exponentially, and here at Quest, we can’t wait to see where they go.

Quest’s Megan Malloy recently sat down with James Ashton to discuss Sailormade’s inspirations, philanthropy, and plans for the future. Anchors away!

Megan Malloy: Tell us a little bit about the genesis of your company.

James Ashton: Both my business partner, Carla Sinatra, and I have had a lifelong love of sailing and of design in many forms.  Being former colleagues at Plum TV, we often spent time walking the docks in places like Nantucket and Sag Harbor admiring the clean lines and beautiful hardware found on yachts in the harbor.

During the fall of 2011, we had an idea for a sophisticated upgrade to the iconic rope bracelet using a Brummel hook, a smart, great-looking clasp used to string signal flags together.  With a bit of refinement to the design and some great-looking custom sailing rope, we thought we had something that people would respond to, and we were right.  Sailormade was born. 

MM: What has sailing come to mean to you and your famiy?

JA: Sailing is one of the best ways to find peace from our crazy lives by detaching from shore and seeking out adventure. During my childhood, learning how to sail on the Connecticut shore, I realized that setting out on the water taught me self-reliance and a great appreciation for our natural environment.

MM: What intially inspired you to incorporate sailing motifs into wearable art? Did you see a niche in the market for yachting-inspired products?

JA: It was a combination of inspiration and what we believe is a niche in the market. There is an inherent beauty and timelessness to designs found in the sailing world, from the polished brass hardware on a classic yacht to a sun-bleached breton stripe tee shirt. We felt that there was niche for a more sophisticated approach to nautical style, one that we like to call “marine modern,” which would appeal to both a classic and fashion customer. Often we find the execution of nautical style to be a bit clichéd, so we aim for a more subtle, stylized approach. We always start with original, authentic marine hardware and materials and then add some refinement to make things we are proud to sell and would wear ourselves.

MM: Where do you see your company expanding in terms of your products and your audience?

JA: At Sailormade, we are excited to be building a lifestyle brand through expansion into other accessories, with an eventual eye to apparel. We aim to create smart, refined, and classic designs for customers who appreciate quality and see beauty in the details. This fall we are launching a collection of leather, rope, and webbing belts that incorporate some new yachting hardware inspirations for both men and women. We are also committed to sourcing and manufacturing in the U.S. wherever possible.

MM: Your company is committed to giving back; tell us a bit about your efforts to make sailing more accessible for the public.

JA: Part of the excitement of building our own business is being able to share our success with causes we care about. Although we are still at a very early stage, we partner as much as we can with fundraising efforts for public sailing centers that offer free access to sailing and affordable instruction to kids and adults.  We believe sailing teaches us skills that we can integrate into all aspects of our lives and an appreciation for our fragile environment.

MM: What pearls of wisdom would you give to an entrepreneur looking to break into the retail industry?

JA: Be ready to make your business your lifestyle at least for the first few years.  Be sure you are creating something that truly inspires you first because that’s what will keep you going during the extremely challenging rollercoaster ride of starting a business!

Sailormade is sold online at and in specialty shops in New York City, Greenwich, Southampton, East Hampton, Locust Valley, Nantucket, and Martha’s Vineyard, among many other domestic and international markets.