The white sugar sand and idyllic blue waters of the Caribbean certainly live up to the paradisal expectations seen on postcards. With lively island hangouts aplenty and serene coves to relax in, your day to nightwear will be anything but formal, but you will need a plethora of decadent swimwear and accessories. Island wear doesn’t need to consist of beige linen pants, floaty sundresses, and straw hats – leave your plush kit at home and get ready to make a casual statement instead.

Blue Lagoon Heaven

Start your Caribbean journey in Anguilla by diving into a colourful reef swim where dressing won’t require much effort at all. Don’t get us wrong show off your energetic side with a bold print while you unwind and destress. The Johanna Ortiz Cerca De La Tie front ruffled swimsuit features ruffles falling from the bustier for an ultra feminine silhouette. Whether you’re in the spa or at the beach you’ll look refined and put together. For something to cover up between swims the Frame Denim Belted Linen-blend shorts will do just that for a relaxed and intricate style that is ideal for a seafood lunch pitstop. Complement your seafront look with a pair of Salon Miste Raffia Slides by Carrie Forbes, handwoven from beige raffia and lined with a navy trim for a timeless style when island hopping.

Frescobol Carioca

Paradise Apagelo

The British Virgin Islands are North America’s answer to paradise that is sprinkled with lush flowers and blue lagoons that never grow tiresome. After a morning of swimming through crystal clearwater caves and snorkelling reefs; stopping for a delicious bite to eat is not hard to find at either Brandywine Estate or The Dove. Pop on a pair of Mr Leight’s Marmont Round frames if the sun gets too much. Made from acetate with a gray mirror lens that lends itself to an air of cool, much like the surroundings.

Give summer wear a creative nod with a pair of linen shorts by Frescobol Carioca. Made with lightweight fabric for maximum comfort and movement, the subtle texture complements the backdrop of bright hues and flocks of pink flamingos. Once you work up a hunger, make a stop on Virgin Gorda where Bitter End Yacht Club will serve up a succulent meal to satisfy your appetite. Pair your seersucker shorts with Onia’s Shaun Jersey Polo that is breathable with a relaxed fit for a failsafe smart-meets-casual choice.

Orlebar Brown


Known as the Caribbean’s destination for sun-deprived Americans, the Bahamas offer sundown like no other. Comprised of over 700 islands and 2400 cays the destination speaks for itself as a place for complete relaxation. If sneakers aren’t your thing but you don’t want to go overboard on fancy footwear here, Want Les Essentiels Heras Leather Espadrilles evoke an affable European style this side of the pond. Blending canvas with leather marrying comfort with versatility.

If you’re a lively soul or down for a tranquil dinner, seersucker pants for an island getaway on Turks and Caicos are both a practical and sophisticated option. Made by Club Monaco, the Lex Slim-fit Tapered Melange Linen-blend Trousers are the perfect smart-casual style that can be dressed up or left to do the talking for you. Waters here are as blue as they come with an abundance of watersports to entice even the least adrenaline-filled junkies out there so be sure to pack the best swimwear you can. Orlebar Brown’s graphic swim shorts speak for themselves for someone who’s ready to hit the ocean.

St. Lucia, surrounded by impressive twinkling skies, balmy sunsets and live music it’s no wonder locals slip into something comfortable that oozes sprezzatura come sundown. Maison Alma’s Exclusive Tie-detail Printed Poplin Top does exactly that – designed on tropical-folage printed cotton, you’ll keep the evening chill out with the matching pants whilst still look fabulous. Rendered in acetate the Bottega Veneta Tortoise-shell Square Frames hold depth whilst still being maintain a neutral palette to compliment your sunset style.

Vivacious Vitalty

Vibrant in tradition, each corner of the Caribbean has its own flair to offer. Sprinkled in beautiful seduction, Antigua boasts gelato-shaded facades against a dramatic backdrop of three volcanoes. With a natural laid-back vibe yet oozing with life and soul, your wardrobe shouldn’t say anything less. Throw in some raw accessories with the Janessa Leone Jodi Straw hat that features a wide brim to keep the sun out and your style in check. Finish off your island look with the Rebecca de Ravenel ‘I See Stars’ Gold-Plated Crystal Earrings that glitter as much as they do shine for your day to night look.

For the man who lives on island time, and as you should be in the Caribbean, to go from relaxing, to the waters, to night in one easy dive, the Panerai Submersible Automatic Goldtech and Alligator 42mm Watch will do just that. Combining copper and platinum for a red-gold finish the sleekness of this timepiece complements your waterfront holiday as much as it supports you below the surface.