How to Dress Like You Own a Boat

I don't often find myself on a boat, but I've had at least two experiences that taught me enough about how to dress while on the high seas. The first was in my youth. It was a crisp autumn day and we were sailing around Long Island Sound. This was my first trip on a boat and as fate would have it, I slipped. My reflexes kicked in and I grabbed the side of the boat while my legs dragged in the freezing water. After getting back on deck, my corduroys were completely soaked and my legs felt like ice. I had to walk through the yacht club with my legs through the sleeves of my jacket. Miserable.

The second was in my adulthood, while sailing in Brazil with the Puma team during the Volvo Ocean Race. Now, these dudes aren't your typical boat enthusiasts—they're hardcore sailors and they go from country to country without thinking twice. Needless to say, a nautical striped sweater didn't fare too well with them and I almost instantly felt like the biggest ass in the Southern Hemisphere. Take my advice and go easy on nautical stripes when you're out there.

But anyway, what's all this info good for if we don't give you a few tips on how to dress like you own a yacht, sailboat or speedboat (even if you don't)? Click through to shop and style yourself like a master of the seas.


Make no mistake: if you're on a sailboat, you're gonna get worked. Sailing is not for the lazy—you'll be moving around a lot and working your arms like a beast. You best watch out for the boom too.