Ralph Lauren on His Jamaican Winter Escape at Round Hill
When I was a kid, I always looked forward to summer because I could go out and play ball and go swimming. Then, years later, I discovered Jamaica. In the middle of winter, I could step out of time. We came there on holiday as a young family more than four decades ago. It wasn’t long before we moved into a romantic old villa on the highest point of Round Hill, a resort overlooking the Caribbean. We called it High Rock. It had a spirit and a glamour that harkened back to the days when Grace Kelly, Noël Coward, the Astaires, Errol Flynn, and Ian Fleming wintered there—there was a timelessness that we loved.
Surrounded by a jungle of trees and flowers, it was our own Garden of Eden. With our children growing up, we needed more space, so in 1997 we purchased Cottage 26 and renamed it White Orchid. Perched right on the water, the cottage was just a short walk down the hill. While High Rock has a classic feel, White Orchid is clean with a barefoot kind of luxuriousness. With a horizon of sky and water all around, it felt like being on a boat.
Sometimes dressing up for no particular reason is reason enough, especially on a balmy evening on the decks at White Orchid.
There’s a naturalness and ease of living here that I love. This is the kind of place you can feel comfortable in. You just get here and think about the water and the air, and then you put on a pair of shorts and go for a swim. There’s nothing formal, nothing complicated. My life here is about rejuvenating, a sense of quiet, a sense of privacy. Every time I come here, it’s like the first time.
When I first started attending black-tie events, I never totally felt like myself. Then one night I decided to mix my tuxedo shirt and jacket with jeans and cowboy boots. I remember some people were shocked, but I felt good—I felt like myself. Now things are different. Today, whether at a private party or on the red carpet, showcasing one’s individual style through what we wear is not only accepted, but what’s expected.
When I’m at our home in Jamaica, there are evenings I dress up, not necessarily for a party or because it’s expected, but just because I’m in the mood for something different. After a day in the sun, choosing to wear a crisp white pleated evening shirt with cuff links, then slipping into a beautifully cut dinner jacket and trousers, barefoot instead of in cowboy boots, feels cool. You never know who might show up—James Bond, perhaps?
Reprinted from © Ralph Lauren: A Way of Living (Rizzoli New York, 2023), the style titan’s book featuring his residences and commemorating the 40th anniversary of the brand’s home collection.
This article originally appeared in our November/December 2023 issue.