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A Conversation with Sunswell Founder Craig O'Brien

Tell us about the idea behind Sunswell
The whole brand is built around the idea of less clothes that do more. The collection is intentionally edited for the guy who knows what he likes, and, when he finds it, he buys 5 of them so he can get back to what he really wants to focus on.
And for your guy, that’s life on the East End?
That’s certainly where we pull our own inspiration...the water, the farms, the fact that you can surf in the morning, then clam for dinner. It’s a small town life that gets a bit of excitement for a few months each summer, and we love that side of it too. 
But it’s really about a release from the everyday, the freedom to pursue your favorite activities with very little in tow, and the knowledge that you will be ready for the unexpected.
You talk a lot about comfort that performs-what does that mean to you?
Comfort is not only about the way a garment feels, it’s about the way it makes you feel. Our Anywhere Short is the perfect example of this. It feels like you are lounging in boxers or surf shorts, but throw on a button down and you can instantly look buttoned up for a night out.
The fabrics are key. We tried so many combinations before we landed on this blend for the short. The poly gives it breathability and keeps it lightweight, and the cotton gives you the classic comfort of summer. Stretch is definitely there as the new standard, and we did a mesh pocket to keep it light.
What drove you to start the brand?
I started my career at Vineyard Vines. I was the second employee and first designer, then spent 15 years with the brand. It was amazing to be part of something that went from two brothers selling ties on a boat to a household name. But for everything we did together and everything I learned from that experience as a whole, my favorite times were the growth points.
So when we moved to Sag, I started working with brands that are in hypergrowth mode, and began developing Sunswell. Of course I love the development and design, but right now what I really enjoy is meeting customers at pop ups, packing orders, all of the super start up stuff that means you are really creating something.
How did you come to be based in Sag Harbor?
When I first came out here in 2007, we rented a house for a week because my wife had a client event here. When we asked her client where to rent, she said we “seem like Sag people” so we tried it. In my first 48 hours here, I went to the farmer’s market, got some local fish to grill, had drinks at the American hotel, swam at Long Beach and surfed in Montauk. I told my wife this was my “place” and we would live here one day. Luckily it all came together somehow.