Winter is dead. Long live spring/summer with the promise of lighter nights and sticking one leg out of the duvet at night. But the real MVP of this seasonal transition is booking a holiday and planning the outfits you’ll cram into your weathered Samsonite, frantically hanging them in your accommodation’s bathroom, hoping the shower steam will sort the creases (does anyone iron anymore?).
Here are a few island destinations on Esquire’s radar for 2023, as well as the styles that fit the vibe of each city.
Sicily, Italy
If the latest season of The White Lotus has got you positively feral for fresh pasta with giant clams, decadent yacht soirees and tanning poolside at a palatial villa, then Sicily, located at the toe of Italy’s boot, is the destination for you.
You may get lost in the island’s luxury offerings but don’t forget to take in some of its historic locations — even if it’s just to come across as cultured to your 677 instagram followers — from the Temple of Segesta to active volcano Mount Etna.
But before posting to your socials, you’ll need to plan the right 'fit. Channel your inner Cameron Sullivan with a pair of cream linen shorts (be wary of spaghetti stains), bold knitted polo shirt and quilted loafers to truly live la dolce vita. And don’t forget the accessories: a pair of polarised sunglasses and a braided belt. You can leave the straw hat at customs, though.
Crochet-Look Resort Shirt
Regular Fit Chino shorts
Quilted Mule Loafers
Polarised Sunglasses
Elasticated Fabric Belt
Valetta, Malta
Three things are inevitable in life: taxes, death and being invited to a wedding in Malta. Since 2015, international nuptials on the Mediterranean island have risen year after year, and that number does not look to be slowing down. If you do find yourself with an invite, see it as a blessing rather than a curse, as Valletta, its capital city, is a history buff’s dream, brimming with baroque landmarks such as St. John’s Co-Cathedral, Grandmaster’s Palace, and Casa Rocca Piccola. For a break from the culture, gorge yourself at Is-Suq Tal-Belt Valletta Food Market, home to some of the finest ice cream, olives and seafood you’ll ever experience.
Anyway, we digress - back to the main event. Abroad weddings are usually more casual when it comes to attire, so take advantage and ditch the tie in favour of an open collar striped shirt, worn underneath a copper suit crafted in linen, a lightweight fabric that’s durable as it is breathable.
Regular Fit Linen Jacket
Short-Sleeved Lyocell Shirt
Linen Suit trousers
Chunky Loafers
Santorini, Greece
Santorini continues to be Greece’s number one destination, mostly thanks to its pristine weather, plentiful and affordable gyros, fantastically crisp drinks, infinity pools, and fairytale sunsets that require zero phone filters.
Another highlight of the island is its quaint white buildings, painted as such to reflect the heat that hammers its rugged landscape. Take inspiration from this practical approach to easy, sweat-free living and opt for a beige but beautiful ensemble consisting of a revere collar linen shirt, knitted vest, and loose-fitting pleated trousers. We don’t know any traditional Greek lingo, so let’s just say ‘PHWOAR’.
Regular Fit Resort Shirt
Hole-Knit Sweater Vest
Regular Fit Terry Joggers
Chunky Trainers
Santa Eulalia del Riu, Ibiza
When we say Ibiza, we don’t mean sweating at a rave with questionable fire safety regulations. We mean IBIZA: fine dining, private beaches, art galleries, designer boutiques et al. Santa Eulalia del Riu is a quieter, luxurious town where you can enjoy the aforementioned list, which has renowned hotels that offer suites with private pools and sea views, spas and your own airport chauffeur equipped with a white Land Rover.
To mirror the stunning landscape of the White Island, pack a lightweight printed holiday shirt. This will be the star of the show, so you can keep everything else simple yet suave. A pair of black chino shorts, crossbody bag, leather mules and a linen cap to keep your cranium cool will finish things off nicely.
Short-Sleeved Lyocell Shirt
Regular Fit Chino Shorts
Small Shoulder Bag
Cotton Twill Cap
Terry Slides
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