Take a Break from Reality This Winter

Perhaps cover your eyes and pick a destination at random. Or maybe just book whatever happens to be in concert with your credit card points. It’s time for sunscreen and sunglasses—and maybe even a new carry-on.

The Tumi Black 19 Degree Aluminium Continental Carry-On Suitcase is the perfect companion to pack in a rush because you waited for inspiration to strike to begin packing. If you’re of a more colorful persuasion, the Monos Carry-On Pro Plus Suitcase has all the bells and whistles of a first-class carry-on, including a four-stage telescopic handle and anti-microbial recycled polyester lining in a calming shade of sky-blue. The Floyd Purple Cabin Suitcase recalls the days of enjoying an in-flight cigarette with vintage-inspired polyurethane 360-degree spinner wheels.

Have you booked your waxing appointment? It’s time to add a little color with a bathing suit that will pop against a tan. New, satin textures from Isa Boulder add a delicate feel to oblique shapes and playful details. Get stuck to a plastic pool chair in a robin’s-egg-blue bikini by BELLE the Label, detailed with graphic stars for a pop of indie-sleaze attitude. Enjoy a fishbowl cocktail the size of your hopes and dreams from the resort’s swim-up bar in a cool-toned pink one-piece by Hunza G.

From Havana to the Hamptons, a great pair of trunks is a key investment in your vacation satisfaction. Channel a David Hockney vignette with peach swim shorts by Casablanca embroidered with a graphic summertime motif. Get cozy near the equator in printed styles, including a vintage-feeling mint-green striped suit from Maison Kitsuné, some classic canvas from Orlebar Brown, or get provocative with a playful trompe-l’œil plaid print from Praying.

Clicking your heels twice with this sandal selection will certainly take you far from home. Speed up the summer solstice with hot sandals for you and Toto, given Toto likes AURALEE. Channel something sweet and Judy Garland-esque with the baby-blue gingham Brigitte Mule Heeled Sandals from Staud. Camp counselor-core takes shape in the collective style consciousness with sandals eager for a hike or a vicious game of frisbee from Miu Miu and Bottega Veneta. The classic leather fisherman sandal gets a minimalist facelift with the Black Tee Cage Flat Sandals from Proenza Schouler.

The beauty of a winter holiday is being able to pass out in the middle of the day. While some may opt for a half-read New Yorker greasy with sunscreened fingerprints to shield their snoozing face, you have the best in hats to keep your moneymaker out of the sun. From Marni, the bucket hat is back and better than ever, adorned with a frayed denim edge and floral appliqué. Pledge your devotion to Paloma Wool in a cotton twill cap in a cool, slate gray, perfect for both managing your air of transitory mystery at the airport and keeping your cool surfside.