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When we head to the water to relax, we are, in many ways, returning to our natural state. Of course, our natural state requires a lot of planning: covering every inch of exposed flesh with SPF in the hundreds, selecting a novel that’s impressive but not too taxing, drinking a rosé that’s the exact shade of pink you associate with the South of France. Then you have to swim a series of laps with perfect form and return to your towel without breathing too heavily. Yes, it’s all very relaxing. But just because beach going requires the planning of a military operation doesn’t mean that dressing has to be complicated as well. I’m always surprised when I see people heading to the beach in clothes that exclaim, “We’re going to have a good time even if we die trying.” These are clothes — bold colors, dizzying patterns, the occasional misguided paisley — that people would never wear in their daily lives but seem ready to experiment with in sight of water.

My suggestion for men heading out into the waves is to take a deep breath and, yes, try to relax. Here’s a thought: Buy a linen overshirt or a chore jacket. This is surprisingly useful and sets the right tone. You’re an adult, not a spring breaker looking for the nearest keg. This jacket can be the soft marine blue typical of French work coats or a gentle tobacco brown or even off-white. But it expresses the fact that you are arriving at the beach, you drive a car or walk there, you might stop at a cafe for lunch. British haberdashery Drake’s has lovely options. This gives you the right touch of panache; if you’re walking around a resort in a dusty pink jacket, you could create an air of mystery. 

Since you’re relaxing at the beach, it might be a good time for some gentle — and I mean gentle — experimentation. Every year, I’m more intrigued by shirts with banded collars. The great Italian designer Massimo Alba swears by these, and I think it’s time for me to give them a try. They are low-key and perfect for lunch at one of the Ischia beach clubs that Mr. Alba frequents. Linen is a good choice here as well. And don’t worry about the first few wrinkles; the shirt looks right when it has a gentle veneer of wrinkledom all over. As you shed your city self, the furrows migrate from your brow onto the shirt. Give it a chance!

Illustration by Hilbrand Bos

Now we all love an espadrille, a true gift of beach life. You can never go wrong with an old pair. And don’t let designers convince you to buy expensive ones; it’s easy to find them online for the price of a paperback book. It’s also a good idea if you ever come across espadrilles on your travels to buy as many pairs as you can. You’ll be happy you did.

Recently, I decided to get a bit more formal with my beach footwear. I found some old Belgian loafers that were in a state of disrepair. These served me very well in Italy. I enjoyed it so much, I wore them to the pool and felt very regal. Do you have any old tasseled loafers sitting in retirement in the back of your closet? Bring them out! It’s a little dash of style on the waterfront. What, these old things? If you want to get more serious about it, Tod’s driving shoes come in a variety of lovely colors and are so soft you’ll never want to take them off.

This feeling of habit is good for vacation dressing. It’s nice to have one item that seems like a tradition. Do you have a favorite straw hat that’s slightly frayed? A pair of Ray-Ban wayfarers your grandfather gave you? An old tote from your favorite store in Tokyo? Even a towel you stole during your honeymoon in Morocco is a nice touch.

This leaves us with one important decision: the bathing suit. My feeling is that the center of my body is where I want to draw the least attention. I like Fedeli bathing suits (a wonderful Italian company) or a pair of more sober Patagonia board shorts. But I am at an age where I don’t want to get too whimsical around my waistline. I’ll defer to you if you’re an underwear model and proud of your sit-up regimen. For the rest of us, a pair of swimming trunks that approaches the knee is probably just right. Now that you’ve done all the planning and hard work that a well-dressed vacation requires, all that’s left to do is go forth and dive in. 

A Minnesotan turned New Yorker, David Coggins is the author of the New York Times bestseller Men and Style and writes a style column for Artful Living.

Read this article as it appears in the magazine.

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