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Style and the Sea

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Style and the Sea

I knew basically nothing about boating when I bought my first boat back in 2015. In fact, the first boat I bought was 2 inches too wide for the lake and I never even got to use it. Sold it. Bought another one. And, long story short, by the end of the year, I had paid about as much in repairs as I had for the boat. I ran out of gas all the time. I always forgot to turn the bilge pump on when it rained so it almost sank while tied to the dock on numerous occasions. But eventually, I figured it out, and added a double decker party barge pontoon boat to my fleet a couple of years later. 

This, mind you, all took place on a lake in Indiana where the waves only got so big and you could almost always see the shore.

Still, when I moved to Puerto Rico, I felt my extensive boating experience would easily translate to the ocean with me at the helm of my new live-on-board 44 foot Sea Ray 400 with two cabins and two bathrooms. It’s a big ocean. Can’t be all that hard not to hit things, right? But as it turned out, that was the least of my worries. I quickly learned you can’t just dock in another country and go ashore, those flags actually mean something and don’t get me started on buoys. As it turned out, I didn’t even know what to wear.

It took a while, but I finally figured out that boating is all about linen shirts and board shorts. At first, I thought a nice cotton T-shirt was the answer. And a pair of Bermuda shorts so I’d look good. But, funny thing about boating on the ocean is you get wet constantly. Rain. Waves. Ocean spray. Avoid all that, and you get thrown in the water by a friend. But linen is perfect. It dries very quickly, especially with the ocean breeze constantly blowing. Plus, it looks good and it’s light.

Like any other new wardrobe, it took time to nail the whole thing. Afterall, my goal was never to just go out to sea, anchor for a while, and head back. I wanted to explore the Carribean and beyond. So that meant having the right clothes for the boat, and for the land. For day. Night. Parties. And even, yes, meetings. So many occasions, so little space. But eventually, I got it down to a science.

I usually pack 2 linen shirts per day because you sweat a lot when you’re out in the heat and the sun (basically, just one more way you get wet). Most of the linen shirts I bring are white, as they’re cooler. I also mix in a few navy blue and denim-colored ones so I have something appropriate to wear when I take the tender boat to shore to go out at night. Or even just to visit a beach bar.

When it comes to swim trunks, I tend to stay with pastel colors for day, which look great with white linen, and mostly grays and browns for later. At night, I wear my more versatile gray or brown board shorts that also look like normal shorts. I don’t pack any underwear, as board shorts serve as utility coverage for both on the boat, and out at night. Another benefit to keeping with linen and board shorts is that they’re easy to wash, and they dry quickly in the breeze and sunshine. 

Shoes are simple. If I’m on a beach, I’m wearing flip flops. But that’s the only place I wear them. It’s not classy to walk around anywhere else in open toed shoes. Not for a gentleman, anyway. On the boat and out at night, it’s Sperry boating shoes. They are bohemian in look, and versatile during both day and night while island hopping.

There are two other items I have on board, just in case a meeting pops up, or I find myself heading to a 5-Star restaurant, and that’s a pair of 18th Amendment linen trousers and my skull slippers. 

I’ve still got plenty to learn about boating. And lots of stories to pass on in future blogs. But at least I’ve figured out what to wear. Like I said earlier, it’s all about linen. But it’s really all about keeping it simple, and doing it with style.

Stephen Schweickart

CO-FOUNDER