Antigua’s year-round sunshine and the Round the Island Race draws a crowd each season looking to enjoy the exhilarating sailing and the white sandy beaches.

The jet set itinerary for Antigua is an enviable mix of beaches, bars, boutiques and boats, calling for a casual travel wardrobe. The island’s relaxed vibe means you can leave the 6-inch heels at home, and revel in a more manageable – yet equally chic – wardrobe.

Enjoy assembling bright colors, loose cuts and luxuriously light fabrics with a selection of high-quality accessories, and roam Antigua in style.


Winter in Antigua doesn’t really count as winter per se, however covering up a little more at the seaside may protect you from late afternoon breezes. Michael Kors has produced a collection of swimwear that screams luxury with its elegant yet edgy cuts.


A fabulous sunhat is a statement well worth making. A wide brim will protect you from the rays, but more importantly, will top off your ensemble with style: be it a sundress or a bathing suit. The cheeky designs from milliner Eugenia Kim, adorned with clever phrases such as ‘Do Not Disturb’ or ‘Greetings from…’ add a fun twist to your look.


Designed in New York City and handmade in Italy, Illesteva sunglasses a favorite with celebrities and fashionistas alike. Illesteva frames are the absolute ultimate when it comes to eyewear, combining classic style with contemporary flair. Whether you’re hitting 5th Avenue or relaxing on a palm-fringed beach, there’s an Illesteva frame to complete your look.


Flat sandals don’t take up space, so indulge and select a few pairs for your trip to Antigua. The casual day-to-play vibe of the island means flat sandals are absolutely acceptable in the evening, and you’ll be surprised how many designers understand and accommodate this jet set requirement. Add a little sparkle to your step in the evening with beautiful crystal or metallic embellishments, and for days spent strolling in the sun and sand, indulge in buttery soft leather.


Laidback island wear is the order of the day in Antigua, but style is not to be compromised. Feminine, floaty dresses are perfect for days in the winter sun made from luxuriously light cotton. The Porcelain Panelled Smock Dress from Zimmermann is the epitome of the little summer dress – intricate detailing giving depth and texture to an effortlessly chic look.


A tote to rule them all is exactly what you’ll need for your time in Antigua: finding a bag stylish enough for sailing, shopping, sunbathing and sightseeing could be a challenge if you haven’t discovered Kayu. Handcrafted from natural materials, Kayu bags bring to life the spirit of adventuring with style. The St. Tropez (pictured) is crafted from woven seagrass, and decorated with pompoms adding light and fun to the functionality of the bag. Have your initials monogrammed for a personal touch.



In keeping with the relaxed vibe of Antigua, we’ve placed Orlebar Brown swim shorts on the must-take list. Designed with the idea of being ‘shorts you can swim in’, Orlebar Brown will take the discerning gentleman from poolside to a casual dinner eliminating the need to change – giving him not only more holiday time, but also more suitcase space. Olebear Brown shorts have received the ultimate nod of approval – they’re Marc Jacobs’ shorts of choice.


Illesteva frames are a great option for gents as well, however if you’re not a his&hers type of couple, gentlemen won’t be hard pressed to find a stylish alternative in the Oliver Peoples range. Distinctive and unique frames are handmade in California and are recognised for their superior polarized and photochromic mineral glass sun lenses – perfect for days on the yacht.


George Clooney wearing Oliver Peoples Linford sunglasses | Christian Louboutin for Casual Day Wear


Is there anyone immune to the charms of a scarlet Louboutin sole? Didn’t think so. A pair of sneakers that will take you in style from the city to the seaside is an essential in any sophistacted travelling man’s wardrobe. These Louboutins are smart enough for travelling first class, and casual enough for strolling the decks: you have comfort and style laced up!


What better way to strike the balance between casual and classy than a relaxed-fit shirt from Ralph Lauren. The gingham shirt is a classic from the fashion house, and with an open neck and rolled back sleeves, gentlemen will achieve vacation chic in seconds. Team it with chinos for a casual dinner, or break with convention and wear it over swim shorts for après beach drinks.


A backpack casually slung over the shoulder doubles as a fashion accessory, when it’s as luxurious a design as those from Santiago Gonzales. Crafted in Colombia from crocodile leather, this bag is tough enough to stand the sun, solid enough to maintain its shape and stylish enough to be a gentleman’s constant companion throughout his time in Antigua.