Resort Outfits for Winter Getaways

The snow boots stay by the door. You pack one suitcase, wear your heaviest sweater on the plane, and by the time the shuttle reaches the resort, you are already thinking about which bag goes to the pool. This guide covers three outfits that carry most winter getaways: the pool day, the afternoon in town and dinner. Then a short packing plan so all of it fits in one bag.

Start With the Weather You're Flying Into

A warm escape in December still has its own rhythm. In Cancun, for example, the average December high sits around 82°F and the average low around 69°F, with sea water close to 80°F all month. Most days are humid, too.

So plan for heat at noon and a softer evening. Loose, breathable pieces do the daytime work. Keep one light layer, a linen shirt or a thin knit, for the walk back from dinner when the breeze picks up.

Outfit One: The Pool Day

This is the outfit you will wear most, so keep it simple. A swimsuit, a cover-up you would happily wear to lunch, a sun hat and flat sandals you can kick off at the lounger.

The cover-up matters more than it looks. Some resorts ask you to cover your swimwear at their casual restaurants, so a shirt dress or a loose linen set saves a trip back to the room at noon.

• Pick one big tote for the day: towel, sunscreen, a paperback, a dry layer for later.
• Give small things a home inside the bag, so the room key never ends up under the towel.
• Wear the hat on the walk down. Hats are easier to wear than to pack.

Outfit Two: An Afternoon in Town

Market stalls, a ferry, a long lunch somewhere with plastic chairs and good fish tacos. Afternoons off the resort call for clothes you can walk in for hours.

Try wide-leg linen trousers or a midi skirt with a plain tank, flat sandals and a small crossbody bag. Keeping your hands free makes everything easier, from paying at a stall to holding a cold coconut. Leave the big tote behind; it gets heavy by the third street.

Outfit Three: Dinner

Resort dining often comes with labels: casual, resort casual, or evening attire. They change from restaurant to restaurant, sometimes within the same property, so check the label before you book a table.

• Resort casual: cover the swimwear, and sandals or flats are usually fine. If dinner is on the sand, flats or sandals make the most sense.
• Evening attire: a little dressier. For women, heels, wedges or dressy sandals work well. At Sandals resorts, for example, men are asked for long pants, a dress shirt and closed-toe shoes.
• Where evening attire is requested, flip-flops and hats can be off-limits, so leave both in the room.

A slip dress or a linen midi, a small shoulder bag with just the essentials, and one pair of shoes with a little height cover almost every dinner on the trip.

Packing It All Into One Suitcase

The trick is a short palette. Cream, sand, white and one darker neutral mix with each other, so every top works with every bottom and every bag works with every outfit.

• Two or three swimsuits and at least one cover-up.
• Two bags: a roomy tote for the day and a small one for the evening.
• Three pairs of shoes at most: flats for the pool, sandals for town, one dressier pair for dinner.
• One hat, worn on travel day.
• One light layer for the plane, cool evenings and air-conditioned rooms.

Wear your bulkiest pieces on the flight and leave the winter coat in the car at the airport if you can. You will not miss it.

Shop the WOTOH Edit

For the pool day: Large Woven Resort Tote, with a detachable zippered inner pouch for the small things.

For the walk to the beach: Woven Wide-Brim Sun Hat, in black or white.

For dinner: Woven Pouch Shoulder Bag, small enough for evenings and day trips.

For a dressier night: Ankle-Strap Espadrille Wedges, with a buckled ankle strap.

Still building the getaway bag? Browse the full WOTOH beach bag collection and pick the one that goes to the pool first.