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Whether you’re planning a tropical getaway or are staying put poolside, one thing to consider as we approach summer is how to maximize your time at play. Who doesn’t want to spend a leisurely day in a swimsuit and then glide effortlessly into evening plans? With the right wardrobe, this is more achievable than you might think. “Look for beach cover-ups that can pull double duty,” Toronto-based stylist Tricia Hall says. “Lightweight and loose-fitting tiered dresses, tunics and even shirt dresses pack light and are versatile.” Stick to this ethos when it comes to shoes, too, and seek out elegant flat sandal styles that can be carried in your beach bag (and will swap out your flip-flops come cocktail hour).

Patterned pieces exude a relaxed and playful vibe, but with the addition of jewellery – the bolder, the better – and an embellished clutch bag, they can also be appropriate for a dune-to-dinner outing. Have fun with your accessories and don’t worry about being too over-the-top. Anything goes when you’re on vacation. “An oversized, lightweight scarf can be used as a chic hair tie or hair band during the day and can be restyled for an evening look when worn around the neck,” Hall says. “[Scarves] can also be worn as hair wrap or turban; this look can work during the day or the night.” Worried about bringing your best silk scarf to the beach? Opt for a less-precious vintage style (they always come in fun, fabulous prints, too).

Look for inspiration from world-travelling trendsetters of the past (Talitha Getty) or present (Jessica Alba and Rihanna) to get your creative juices flowing. But don’t forget – your best guide is a free spirited mindset.

Photography by Renata Kaveh. Styling by Odessa Paloma Parker. Photographed at the Kimpton Seafire Resort in Grand Cayman, Cayman Islands.

Best dress

RENATA KAVEH

A Tanya Taylor piece, in a print that mashes up leopard dots and zebra stripes, buttons up the front, allowing for quick changes between your beach chair and the hotel lobby.

Tanya Taylor dress, US$615 through tanyataylor.com. Left on Friday bikini top, $100, bikini bottoms, $100, through leftonfriday.com. Earrings, $199, bracelet, $549 at Swarovski (swarovski.com). Vintage scarf, stylist’s own.

Spot on

Renata Kaveh

Think of this A Peace Treaty set as a sun-destination power suit. Its bold hue and relaxed cut elevates the personality of more basic swimwear.

A Peace Treaty shirt, US$275, shorts, US$295 through apeacetreaty.com. The Saltwater Collective bikini top, $65 through thesaltwatercollective.com. Vintage earrings, price on request through caroletanenbaum.com. Vintage scarf, stylist’s own.

Cape it off

Renata Kaveh

When you covet a cover-up that’s more about adding flair than actually concealing anything, search out a sheer option that’s as light as air from your local vintage shop.

Ciao Sea one-piece swimsuit, $220 through ciaosea.com. Cape, $145 through facebook.com/NouveauRicheVintage. Vintage earrings, price on request through caroletanenbaum.com. Vintage scarf, stylist’s own.

Robe report

Renata Kaveh

From spa-to-beach, packing a few printed robes lets you stand out in a sea of terry cloth.

Birds of North America robe, $198 through birdsofnorthamerica.com. June Swimwear bikini top, $71.99, bikini bottoms, $64.99 through juneswimwear.com. Vintage earrings, price on request through caroletanenbaum.com. Vintage scarf, stylist’s own.

Skirt the issue

Renata Kaveh

Isy B (a.k.a. Isy Obi) is one of the Cayman Islands’ fashion stars. Her skirt incorporates an original, hand-painted print on a silk-blend fabric.

Isy B skirt, US$435 through isybdesign.com. One-piece swimsuit, $286 at Shan (shan.ca). Ring, $199 at Swarovski (swarovski.com). Vintage earrings, price on request through caroletanenbaum.com. Vintage scarf, stylist’s own.

Tile works

Renata Kaveh

With its combination of colourful motifs, Hilary MacMillan’s spring collection transports you to exotic summer destinations, even if you’re just hanging out on the cottage dock.

Hilary MacMillan shirt, $125, trousers, $135 through hilarymacmillan.com. Andrea Iyamah one-piece swimsuit, US$171.05 through andreaiyamah.com. Earrings, $299 at Swarovski (swarovski.com). Vintage scarf, stylist’s own.

Makeup and hair by Sheri Stroh for Charlotte Tilbury/Plutino Group. Model: Hannah Donker at Elite Model Management. Photo assistant: Derek O’Donnell. The Globe and Mail travelled to Grand Cayman as a guest of The Cayman Islands Department of Tourism. The organization did not review or approve this story prior to publication.

On location: Kimpton Seafire Resort + Spa

Kimpton’s Seafire Resort + Spa flaunts the natural beauty and cosmopolitan vibe of Grand Cayman.Handout

From its expansive penthouse suite, with views all the way down Seven Mile Beach, to its poolside campus of colourful bungalows, Kimpton’s Seafire Resort + Spa mixes the natural beauty and the cosmopolitan vibe of Grand Cayman. On-site amenities include Seafire Supply Co., where you can stock up on even more fashion-focused beach attire by a mix of international brands and local designers, and a lineup of restaurants including taco spot Coccoloba and steak and seafood destination Ave.

The penthouse suite offers views all the way down Seven Mile Beach.Handout

The hotel is a short drive to the bustling capital George Town and the expansive Camana Bay shopping district, or head further afield to some R&R at Rum Point. Room rates from US$499 plus a US$70 daily resort fee through seafireresortandspa.com.

Both Air Canada and Westjet fly to Owen Roberts International Airport in Grand Cayman via Toronto. For more information, see visitcaymanislands.com.

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