Where The Wild Things Are: Tactically Tinged Fashion Takes to the Water—and the Woods—in Maine

I spend summers in Maine, where I was born and raised. Despite this, a yearly aspiration, or yearly delusion, possesses me each June when I’m staring into my Manhattan closet and choosing what to pack. I think, I might wear that cotton dress, or I should really pack those sandals. I won’t and I shouldn’t. Because I’m often outside, in wildly shifty weather—a half century in Maine prepared me to expect the best and the worst, often in quick, cycling succession—I know that neither will ever touch my body. But restriction can promote innovation. As a result, I’ve developed a summer style based on practicality and foresight and to which I also have a deep emotional attachment, because it pays homage to the clothing habits of my childhood. I’m layering my old self over my new.

But I’m also, literally, layering.

Take one recent late-summer day. Invited to attend a party on an uninhabited island a mile offshore, I looked out the window and saw morning sunshine and blue skies and thought HAHAHAHA, then opened the old sea chest where I keep the fashionable multipurpose gear required to survive a typical summer day on a Maine island.

First, I snapped on an old Speedo, because the ocean acts like battery acid on bathing suits and ponying up for a new one is roughly as sensible as tying hundreds of dollars around a rock and throwing it into the harbor. (As I yanked the straps over my shoulders, I received a text report that it was currently hailing on the island.)

Next, I put on a hand-​me-​down T-shirt I got from my friend John, which has holes so perfectly placed that my teen son, a Rick Owens fanatic, regularly comments on its accidental genius. Over it, a Helly Hansen long underwear shirt featuring modernist racing stripes down the sleeves, to provide a bit of visual architecture. Over it, an Icelandic sweater from the ’60s with a funnel-​shaped boatneck high enough to shield me from the elements, nearly to the chin.

Because the sweater is boxy, I tied a Patagonia hooded Micro Puff jacket around my waist like a cummerbund, which could serve as an extra layer if needed. Then I pulled on some bright-​pink-​and-​blue running tights, and over the tights, a pair of men’s madras Bermuda shorts.

This was a summer party, after all.

On my feet, I put a pair of wool socks and shin-high white fishing boots. I packed an extra pair of wool socks in case one wasn’t enough.

Finally, I randomly grabbed one of the two matching foul-weather jackets I inherited from my parents, who, in the ’80s, thought it best to spend summers sailing northward to even colder places, like Cape Breton. The zipper is broken but the Velcro works, and there’s still a safety whistle attached to the hood, to be used in case my dinghy, which I planned to row solo to the island, capsized—which it nearly did, because the wind whipped up—and I needed a rescue.

In my bag I stashed a ski hat, for when it got cold, and a baseball cap, for when it got sunny, because it would get both, sometimes simultaneously.

After battling through a half mile of waves in my dinghy, I arrived at the party. I immediately found myself helping fend a bigger boat off the rocky shore, which meant my boots swamped with ocean water, the insoles chilly sopping sponges now. I would have to go barefoot for the rest of the day, which was fine—by the end of summer my feet have toughened up. Still, once they thawed later that night, I’d find deep slices under my toes that already looked infected. I should have packed a pair of rubber clogs, not just extra socks. Every day in Maine is a learning opportunity.

Then another squall blew through, just rain and wind this time, no hail, and I flipped my dinghy over so that underprepared people could shelter beneath it. My dinghy counted as part of my outfit, the ultimate foul-weather gear, which I was happy to let others borrow.

For the rest of the day, the weather alternated between sunny and stormy, and then it was 6 p.m., and it felt more like fall than summer, but when it’s cold like this the water is paradoxically warm and welcoming, especially after many piña coladas, and so that’s when we went swimming.

Finally, the wind seemed to permanently lie down, though storm clouds still haunted the horizon, forcing the sunset to squeeze beneath them, its rays condensed into a lurid, painterly slash. I rowed home through the Technicolor reflection and reached the dock just after nightfall. I forgot a flashlight, which I could have tied around my waist with a rope. Next time I’ll add it to my outfit, because my layers are always accruing, in response to the wind, the rain, the waves, the dark.

In this story: hair, Dre Demry-Sanders; makeup, Homa Safar.

Produced by Petty Cash. Visuals Editor: Paige Viti.