Meghan Markle's Caribbean Vacation Style, Shopped
From a 2017 Jamaican wedding to a private Caribbean escape years later, Meghan Markle's holiday wardrobe has a clear, shoppable formula. Here's how to get it.
Meghan Markle’s Caribbean vacation style has been quietly consistent for the best part of a decade, long before the wedding, the titles, or the move to California. It is a look built on ivory maxi dresses, a single reliable straw hat, and a determination never to overdress for the heat. It is also a wardrobe that translates: not couture gowns or tiara-adjacent evening wear, but the kind of holiday pieces most of us could actually pack.
There are two documented Caribbean chapters worth studying. The first is her introduction to the world as Prince Harry’s girlfriend, at a wedding in Jamaica in March 2017. The second, years later and worlds away from royal life, was a low-key private escape to the Grenadines. Between the two sits a consistent aesthetic, one part practical and one part quietly glamorous, that has become as recognisable as anything she has worn on official duty.
Below, we trace what is actually verified about her Caribbean wardrobe, be honest about where the paper trail runs thin, and shop the general silhouettes, colours and categories that define the look.
The introduction: Jamaica, March 2017
Meghan’s first Caribbean moment as a public figure came at the wedding of Thomas “Skippy” Inskip, one of Prince Harry’s closest friends, to Lara Hughes-Young. The ceremony took place on 3 March 2017 at the Round Hill Hotel and Villas in Montego Bay, and it marked the first time the couple had been photographed together at a social event, three months into a relationship they had so far kept determinedly private.
For the occasion, Meghan wore a floral silk-chiffon gown by the British-Canadian designer Erdem, reported at the time to cost around $1,500, along with Mykita sunglasses and her Cartier Love bracelet. It was a considered, London-leaning choice for a Caribbean wedding, proof even then that her holiday wardrobe favoured elegant restraint over full beach-party colour. The couple were said to have stayed in one of Round Hill’s private ocean-view villas, with Harry among fourteen ushers at the wedding.
A private island, years later
The most recent documented Caribbean trip came via a paparazzi photograph published in October 2023, showing Harry and Meghan in Canouan, a three-mile-long island in Saint Vincent and the Grenadines known for its exclusivity and its Sandy Lane Yacht Club and Marina. The pair were photographed near Glossy Bay, without their children, and described by an onlooker as visibly affectionate.
Meghan’s outfit that day was, by all accounts, the platonic ideal of off-duty island dressing: an ivory sleeveless maxi dress by Chloé, a matching white Panama-style hat, and a white Goyard tote. Harry kept it simple in a white T-shirt and black shorts. Beyond that single sighting, few further details of the trip have been reported, presumably exactly how a couple who have spoken openly about craving privacy would want it. What the photograph does confirm is that, years on from Jamaica, the instinct toward pale, fluid, unfussy holiday dressing had not changed at all.
A Caribbean bride, long before the crown
Meghan’s history with Caribbean beaches predates Harry by six years. In September 2011, she married her first husband in a four-day beachfront celebration at the Jamaica Inn in Ocho Rios, with beach games in a bright yellow bikini and a barefoot reception on the sand. It is a footnote rather than a style chapter, but it explains something real: long before she was a royal fixture, Meghan already had an easy relationship with warm-weather dressing. The instincts she brought to Jamaica in 2017, and to the Grenadines years later, were not new to her.
The silhouette: ivory, maxi, unstructured
If there is one throughline across every documented Caribbean sighting, it is the maxi dress in a pale, warm-toned neutral: ivory, cream, bone. It is an unusually disciplined choice for beach dressing, where bold prints and bright colour are the easy default. Meghan’s version is almost always sleeveless, floor-skimming, and cut from a soft, breathable fabric that moves rather than clings.
The appeal is practical as much as aesthetic: a pale maxi dress photographs beautifully against turquoise water and white sand, works as easily for lunch on a terrace as for an evening stroll, and requires almost no additional styling to look finished. For anyone building a holiday wardrobe around one hero piece, this is the formula worth copying: a single well-cut ivory or cream maxi dress that can be dressed up with gold jewellery or left entirely plain.
Swimwear: the one-piece over the bikini
Meghan’s most talked-about recent swimwear moment was not, strictly speaking, Caribbean. A 2024 “summer holiday” photograph was taken in Portugal, where the Sussexes bought a home in 2023. It belongs in this conversation regardless, because the swimsuit itself, a simple black one-piece with a scoop back, drew immediate comparisons to a near-identical suit Princess Diana wore on a Caribbean holiday to Nevis in January 1993.
The through-line is a genuinely royal one: a preference for a well-cut one-piece over a bikini, styled with minimal jewellery and a confident, unfussy attitude. Diana’s own Caribbean holidays, in Mustique and the British Virgin Islands through the late 1980s and 1990s, ran to leopard print and bold colour as often as black, paired with matching sarongs, a slightly more playful cousin of the pared-back look Meghan favours today. Either way, the category holds: a flattering one-piece is timeless and never once looks like it is trying too hard.
The hat she is rarely without
No Meghan beach look is complete without a wide-brimmed straw or Panama hat, and this is one area where the paper trail is genuinely rich. She has been photographed in styles from Madewell, Cuyana and Janessa Leoné over the years, favouring natural raffia or woven straw in cream and camel tones with a simple leather or fabric band. The Canouan photograph shows the same instinct at work: a white Panama-style hat doing the practical job of sun protection while finishing the outfit rather than competing with it.
It is, of all her holiday habits, probably the easiest to borrow directly. A good wide-brim straw hat in a neutral tone works with almost anything in a warm-weather wardrobe, packs reasonably flat, and does the one job sunglasses and sunscreen cannot: keeping the sun off your face while looking deliberate rather than accidental.
Sandals, totes and the finishing touches
Meghan’s holiday footwear runs consistently to flat or low-heeled sandals in neutral leather. She has been photographed in thong and T-strap styles from the New York label Emme Parsons, generally in black or tan with simple hardware. It is a sensible category to shop generically if you cannot pin down the exact pair: a clean leather sandal with minimal straps, a comfortable sole, and a colour that goes with everything else in a holiday case.
The accessories follow the same restrained logic. The Goyard tote carried in Canouan and the Cartier Love bracelet worn in Jamaica sit at the luxury end of the spectrum, but the principle scales down easily: one structured neutral tote free of logos, plus one piece of fine gold jewellery that can go from morning swim to evening drinks without a change of outfit.
Why the look endures
What makes Meghan’s Caribbean wardrobe worth studying is not any single dress or hat, but the consistency of the idea behind it: dress for the heat, keep the palette calm, invest in one or two pieces that do most of the work, and let the setting supply the drama. It is a formula that has not changed meaningfully between a wedding in Montego Bay in 2017 and a private island in 2023, and it is one that translates from a royal holiday to an ordinary one without much adjustment at all.
Frequently asked questions
What did Meghan Markle wear on her Caribbean vacation with Prince Harry?
The most documented sighting, in Canouan in October 2023, showed her in an ivory sleeveless Chloé maxi dress with a white Panama-style hat and a white Goyard tote. At an earlier Jamaican wedding in March 2017, she wore a floral silk-chiffon Erdem gown.
Where did Meghan Markle and Prince Harry go on their Caribbean vacation?
The clearest reported private Caribbean trip was to Canouan, a small island in Saint Vincent and the Grenadines, where the couple were photographed near the Sandy Lane Yacht Club and Marina in October 2023.
Did Meghan Markle visit Jamaica before she met Prince Harry?
Yes. Meghan married her first husband, film producer Trevor Engelson, at a beachfront celebration at the Jamaica Inn in Ocho Rios in September 2011, six years before she attended a friend’s wedding in Jamaica with Prince Harry.
What hat brands does Meghan Markle wear on holiday?
She has been photographed in wide-brimmed straw and Panama-style hats from Madewell, Cuyana and Janessa Leoné, generally in natural or cream tones with a simple band.
Does Meghan Markle wear bikinis or one-piece swimsuits?
Her most recent documented swimwear moment, from a 2024 holiday in Portugal, showed her in a simple black one-piece with a scoop back, a style choice that echoed a similar suit Princess Diana wore on a Caribbean holiday to Nevis in 1993.
What sandals does Meghan Markle wear on vacation?
She has worn thong and T-strap sandals from the New York label Emme Parsons in neutral leather tones on several warm-weather trips.
Is Meghan Markle’s Caribbean vacation style affordable to copy?
Largely, yes. The formula relies on categories rather than named designer pieces: an ivory maxi dress, a neutral straw hat, flat leather sandals and one simple tote, all of which are widely available at a range of price points.
What was Meghan Markle’s first public appearance with Prince Harry?
Her wedding-guest appearance in Jamaica in March 2017, at the wedding of Harry’s friend Thomas Inskip, is widely reported as the first time the couple were photographed together at a social event.
Details of Meghan Markle’s 2017 Jamaica appearance and 2023 Canouan sighting are drawn from contemporary press reporting; some specifics of both private trips, including exact dates of the Canouan visit, have not been officially confirmed.
