Column: Not dressed to impress

CHARITY ROBEY PHOTO The height of fashion for Shelter Island.
CHARITY ROBEY PHOTO The height of fashion for Shelter Island.

A strange thing occurred in the summer of 2013. A website called called out Shelter Island as “the chunk of land right smack between the North and South Forks of Long Island, which, if our Instagram feeds are any indication, has become something of a hotspot for the fashion set.”

At the time, I thought it was mysterious (Instagram?) and wrong-headed (how does the fashion set get to a place that stops accepting visitors at midnight?). Since only a few locals were among the 2.5 million monthly readers of, most were blissfully unaware that the Island was a hotspot for anything.

Here we define fashion, like every other aspect of modern life, in our own way. The most important fashion rule seems to be — not too fancy. A few years back I was invited to a get-together with a new group of friends and I asked one of them what I should wear. “We don’t dress up here,” she said severely, looking me in the eye over her readers. I wore jeans and a T-shirt.

Designer and artist Jonathan Adler and his husband, Simon Doonan, of Barney’s New York are the rare combination, Island residents and bona fide fashionistas, so when Adler told W magazine, “Shelter Island is about a rustic modernism and being outdoors,” it had the ring of truth.

He could have been talking about the Island’s summer uniform, a signature look that involves wearing trousers tucked into socks, a practice so ubiquitous it’s easy to forget it started as a way to keep ticks from climbing up your legs on their way to a darker place.

The town supervisor is often seen tooling around town in a blue convertible wearing an outfit that perfectly expresses rustic modernism; the slightly-worn collar on his faded red T-shirt worn under a tattersall shirt that could have been purchased anytime in the last half of the 20th century.

The first and second Mondays in November, the dock at the Congdon Creek Town landing is transformed into a fashion runway with baymen and women parading in vintage scallop-harvest apparel, much of it waterproof.

Dressing up Island-style means something different than in the Hamptons. Setting aside Italian loafers and cashmere sweater, Tim Purtell appeared at the Historical Society’s annual oyster festival sporting a large, pearly shell which hung from his shoulders like a sandwich board, accessorized by silvery gloves that left no doubt he was dressed up — as an oyster.
In November the annual Turkey Plunge took place at Crescent Beach where 10 weeks earlier, beach cabanas sheltered fabulously well-oiled visitors in tiny swimsuits. The Plunge is a chance for Islanders to put it on while taking it off for a good cause, and one of them showed up dressed as a turkey.

Here business casual is camouflage, especially in January. The preferred men’s hat has been a baseball cap (usually plain, without team logos) for as long as anyone can remember, especially since business generally involves working outdoors.

Bill Cunningham, the late New York Times fashion photographer, documented contemporary style by people-watching at 5th avenue and 57th street, and in that same spirit, watching the flow of Islanders in the vicinity of Piccozzi’s Gas Station is a good way to get a sense of Shelter Island style. Flannel appears to be more popular than velvet this holiday.

Another measure is whatever is for sale at Bliss’ Department Store, the only place on the Island that offers a range of clothing for men, women and children. There you can purchase a fleece vest or a pair of sweatpants and, at some point, most of us have.

Also available is a very smart hooded wind jacket, with the map of Shelter Island embroidered on the breast, available in green, navy or yellow, an item that will undoubtedly be under more than one Island Christmas tree.

Many local shins are protected, waterproofed and ornamented by a pair of the high, rubber boots sold at Bliss’. I can personally attest to the excellence of these boots, a lifesaver when I attempt to walk my dog on the beach at high tide on a winter afternoon and she decides to roll in the partially-submerged carcass of a horseshoe crab.

When it comes to exercise, no one is more tolerant of personal style than Islanders. Do you like to run in a large floppy hat and micro shorts? No one will judge you. Do you climb onto the stationary bike in khakis and a shirt with a collar? Enjoy your workout. The only ones wearing spike heels on Shelter Island are the Bucks.

It’s been four years since’s Instagram feed identified the Island as a hub of fashion, and in retrospect it hasn’t caused much trouble. Maybe the fashionable people they were talking about were never really here. Because real Shelter Island fashion has more to do with washing instructions than Instagram, at least until someone opens a dry cleaner. So much for that cashmere sweater.