The charms of a flirty little cover-up are many, but, truth be told, coverage is not among them. And if we’re spending the entire day in the sun, we’d prefer to avoid interrupting our relaxation to slather and then re-slather ourselves with S.P.F. Try a long-sleeved, ankle-grazing caftan for an extra layer of protection. D’Ascoli’s cotton-voile dress is destined to be the belle of the beach thanks to its floral and foliage prints. Handmade in India by local craftspeople, it has much better tailoring—draped balloon sleeves and a clever belted waist—than its price would suggest. ($259, matchesfashion.com)

If you are lucky enough to be heading somewhere with sunny weather this winter (and we sincerely hope that you are), leave your leftover summer sandals behind and pack these all-purpose huaraches from Brother Vellies instead. Founder Aurora James launched the brand to create artisanal jobs throughout Africa while showcasing traditional footwear styles from the region and around the world (these huaraches are handwoven in Mexico). We’re partial to this neutral nutmeg hue, but the romantic blush color is also tempting. ($225, brothervellies.com)

Most straw hats end up crushed, misshapen, and sodden with seawater by the end of summer. So, before you embark on holiday, invest in one you intend to wear strictly on solid ground. While Sensi Studio’s toquilla-straw hat has an extra-wide brim, ensuring maximum sun protection, it’s also flexible and lightweight enough to be stowed in a suitcase without getting crinkled. And the grosgrain ribbon tie ensures that it won’t fly off at the first strong breeze—we’re still smarting over a Brunello Cucinelli number that was lost to the gods in Dubrovnik this way. ($215, net-a-porter.com)

Is there anything more irritating than hauling a mess of thick towels to the beach? Onia’s beach blanket is the perfect solution to the unwieldy playa haul. Made of lightweight, quick-drying linen, it neatly folds up, leaving plenty of space in your bag for the essentials—books, sunscreen, and a bottle of rosé. And outside of beach season, it does double duty as a picnic blanket—albeit one whose palm-tree print will remind you of the tropics, but we could all use a little more reminiscing on that front. ($95, mrporter.com)

Resort season is upon us. If your day is proceeding as it should, you’ll end up lunching in a bathing suit and sarong. The former should be a stylish, modest maillot with a vintage vibe—like this one from Palm swimwear. The brand uses materials such as a high-quality nylon made from recycled plastic and discarded fishing nets to create these stunning and extra-ocean-friendly suits. The Grace maintains its shape beautifully and offers UV protection, but it can also be worn after sundown, paired with a long linen skirt and a light jacket. ($270, goldenedit.com)