Beach Vacation Outfits for Winter Sun, From a Cold Departure to New Year's Eve

Beach vacation outfits for a winter-sun trip have to solve a problem the summer version never meets: you leave a city like New York, where December averages a high of about 44°F, and land somewhere 30 to 40 degrees warmer. Dress for the hot end of the journey and add only warmth you can carry, which means a fine cashmere knit and a short down jacket over crepe trousers or a jersey dress, with flat shoes that also work on arrival. Then pack by moment rather than by garment: a swimsuit and a long-sleeved shirt for the beach, separates that pass at the pool-club bar, a poplin or linen dress for the long lunch, a shirt, shorts and rubber soles for the boat, silk for dinner, and one piece with some shine for Christmas Eve or New Year's Eve.

Below: December weather in eight warm destinations, an outfit for each part of a trip between Thanksgiving and New Year's, and what to buy once. Beach and resort trips are among the occasions people most often bring to our AI stylist, and those requests did not stop when the weather turned: we counted 16 typed beach and resort asks in November 2025, 20 in December and 17 in January 2026.

Winter sun outfits start with the weather

"Somewhere warm" covers very different Decembers. The Caribbean stays warm after dark, Florida cools at night, Los Cabos sits at the dry southern tip of Baja California, and December is one of the wetter months in the Maldives. December averages, rounded:

The New York, Florida, San Juan and St. Thomas figures are NOAA's 1991–2020 US climate normals, read at each city's reference station. Nassau, Cancún and Los Cabos are 1971–2000 averages, and Malé 1981–2000, from the national weather services that report to the World Meteorological Organization's World Weather Information Service. Those periods end more than 25 years ago, so read every figure here as a guide to pack by, not a forecast.

A Thanksgiving trip falls in the last week of the storm season. The National Hurricane Center's Atlantic hurricane season runs from June 1 to November 30, and Thanksgiving is Thursday, November 26. For the suitcase, rain matters more: in the 1971–2000 averages, Cancún has about 12 rain days in November. For a Thanksgiving week there, pack a swimsuit that dries overnight and sandals that can get wet, and leave suede at home.

Los Cabos needs a real evening layer. Its December night averages more than 20 degrees below the day, the widest swing on the list, so pack a cashmere sweater or a long-sleeved dinner dress.

The Maldives asks for coverage off the resort. November and December are among the wettest months in Malé's 1981–2000 averages; February is the driest. If the trip includes a local island, the UK Foreign Office's travel advice for the Maldives asks visitors outside resorts, including on beaches used by locals, to keep their shoulders covered, avoid short or tight-fitting shorts, and keep arms and upper legs covered when bathing. It adds that topless sunbathing is not allowed anywhere, resort islands included. A loose linen shirt dress covers that day.

The transition outfit: leaving a cold city, landing in the heat

The departure outfit goes wrong when it is dressed for the wrong end of the day. Build it from what you will wear on arrival. The base should not crease: jersey, crepe or a fine knit, as trousers or a dress, comes out of five hours in a seat looking better than linen or poplin. Over it goes a fine knit that will also be your dinner layer, in ivory, oat, gray or blush. Then decide the outer layer.

• Driven to the airport: leave the coat in the car and wear the knit with a scarf for the curb and the jet bridge.
• A taxi, a train and a long walk to the gate: a short down jacket, which squashes into a tote in a way a wool coat never will. Moncler's cropped Tepice is listed in lightweight micro ripstop.
• The mistake: a long wool or shearling coat, carried through arrivals and left in a hotel closet for a week.

Board in loafers, ballet flats or clean sneakers you would wear into town at the other end, not boots you will pack for a week, and wear a pair that is already broken in. Put a swimsuit, flat sandals and sunglasses in your carry-on: if the room is not ready or a bag goes astray, you still have the afternoon at the pool.

• Northeast to the Caribbean: ivory crepe wide-leg trousers, a sleeveless silk shell, Bottega Veneta's ivory cashmere-silk bouclé cardigan with its gold brooch closure, the short down jacket and gray suede loafers.
• The overnight flight to the Maldives: a navy knit column dress under Max Mara's long, relaxed wool-and-cashmere cardigan, which you can sleep in, and white sneakers.
• To Cabo for Christmas: Loro Piana's hooded cashmere sweater over a white poplin shirt, cream trousers and ballet flats; the sweater comes out again at dinner.

Choose the knit by gauge rather than warmth: a fine cashmere, cashmere-silk or cotton knit earns its space twice, while a chunky hand-knit belongs in the city you are leaving. Brunello Cucinelli's Monili V-neck is cotton, right for a breezy terrace, and TOTEME's short-sleeved cashmere-silk polo works on board and at a beach lunch. Browse more designer cardigans.

What to wear on a beach vacation: the beach day

A December beach day is about sun more than heat. The EPA's sun safety tips note that UV rays are strongest between 10 a.m. and 4 p.m. and that water and sand reflect them, and recommend a long-sleeved shirt, a wide-brimmed hat and sunglasses. Plan the shade as carefully as the swimsuit: the shirt over the suit is part of the outfit.

For a week, pack three swimsuits chosen for what each day holds. A one-piece with structure goes from the lounger to a beach-club lunch under trousers or a skirt: Zimmermann's black Mahon has beaded, adjustable straps, and Balmain's two-tone suit crosses into a V at the front. A printed one-piece, such as Pucci's one-shoulder suit or Chloé's aqua flower print, hides sunscreen marks and the odd snag from a lounger. A bikini is for the boat and the lounger.

Try new suits on at home with the size chart open. The picks below use at least five sizing systems: Chloé in French sizes from 34 to 44, Zimmermann in its own 0 to 3, Dolce & Gabbana in numbers from 1, Missoni in Italian sizes, and Pucci in letters. For fit, lining and support, see our guide to luxury swimwear; for more cuts, the 25 best swimsuits of the year.

• Pink and white: Pucci's pink one-shoulder suit under an oversized white cotton-linen shirt, a straw hat and white sunglasses.
• Butter and sky: Versace's butter-yellow Medusa one-piece with a pale blue men's-style shirt worn open and rubber thong sandals.
• Orange all day: Dolce & Gabbana's orange jersey one-piece, cut low at the back, with Casablanca's white towelling shorts from the pool-club edit below.

Missoni's fully lined crochet-knit suit is from its Missoni Mare line, and its retailer suggests wearing it as a bodysuit at dinner. Browse all designer swimwear, or our edit of the 25 best beach bags.

The pool club: dressed enough for the bar

A pool club is a whole day in a swimsuit with a bar a few steps away. Our rule: when you stand up, cover your hips. A top over a bikini is not enough; shorts or a skirt over a swimsuit is. Separates do this better than a kaftan, in one of three fabrics.

• Terry and swim fabric go over a wet suit without marking. Casablanca's Waves Monogram towelling shorts are made, the listing says, from a technical swim fabric, and Missoni's zigzag terry crop top and miniskirt are polyester, which dries faster than the cotton of a hotel robe.
• Crochet looks finished at the bar and lets the air through. Zimmermann's Aster top and shorts are cotton crochet trimmed in black and cut as a set; Rabanne's ecru crochet top, with silver hardware, leans toward evening.
• Silk twill shorts are the dressiest choice and the least forgiving, because water marks silk. Put them on over a dry suit and sit on a towel. Pucci's sky-blue Leocorno shorts and Versace's butter-yellow Broken Jewels shorts both have elastic waists.

• The matching set: Missoni's zigzag top and miniskirt over a white one-piece, with yellow rubber slides.
• Cream on black: Zimmermann's crochet top and shorts over a black one-piece, with blush rubber thongs.

Pool decks are wet, and leather soles slip and water-stain, so this is where rubber earns its place. Bottega Veneta's Carpet slides are, as the retailer describes them, pool slides of spongy rubber stamped to look like the house's intrecciato weave. Valentino's Rockstud rubber sandals have, per the listing, a non-slip sole with a lined tread, which also makes them our pick for the boat. Ferragamo's Jealsa, Prada's rubber thong and The Row's plain black Ama slide are the quieter choices, and Jimmy Choo's cut-out jelly ballet flats cover the toes for the walk into town.

The long lunch: a day dress that goes over a swimsuit

The long lunch is the meal a beach vacation is planned around: two or three hours in the shade, usually straight from the sand. The dress goes over a swimsuit, so choose the two together.

• Match the necklines. A halter dress goes over a halter or strapless suit; a square or scoop neck over a suit with straight straps. Crossed straps showing at the shoulder look accidental rather than layered.
• Let a print or a lining hide a damp suit. Pale, unlined linen shows every wet patch. Oscar de la Renta's watercolor-iris poplin dress is lined in cotton, according to its listing, and a busy print shows nothing.
• Midi length stays modest on a low banquette and clear of the sand.
• Mark the waist. A belt or a seam at the waist stops a dress worn over a swimsuit from reading as a cover-up. Oscar de la Renta gathers its pink poplin halter dress with a gold-tone floral brooch at the waist, and Burberry belts its harvest-beige Jessica dress.

• Garden lunch: Oscar de la Renta's belted watercolor-iris dress over a pink one-piece, with gold kitten-heel thong sandals and a straw basket.
• Print at the table: Dolce & Gabbana's gathered Carretto-print poplin midi with flat leather slides and coral earrings.
• Linen with structure: Carolina Herrera's Cabana dress, a floral linen-and-silk midi boned at the bodice, over a suit with straight straps to match its square neck, with gold sandals.

For lunch in full sun, choose sleeves. Gabriela Hearst's Ignis dress, in lightweight linen with a degradé floral print, has short puff sleeves over the shoulders, and Etro's belted floral cotton shirt dress has long sleeves and a collar for the back of the neck. Browse more designer day dresses.

The boat day: sun, spray and a wet deck

Many winter-sun trips include a day on the water: a catamaran to a reef, a lunch boat, a friend's yacht. A private yacht has its own etiquette, which our guide to what to wear on a yacht covers. For any boat, plan for three things.

• Reflected sun. The EPA singles out water as a surface that reflects UV, and on a boat it surrounds you. A long-sleeved cotton or linen shirt over the swimsuit, buttoned at the wrists while the boat is moving, is the simplest protection.
• Wind and ladders. Shorts beat a skirt on a moving boat and on a swim ladder. Zimmermann's Mahon shorts, tailored in cotton with front pleats and a daisy trim at the hem, look smart enough for lunch ashore; TOTEME's silk twill shorts, with an elastic waist, fold small for the swim stop.
• Wet steps. Wear rubber soles with some grip rather than leather, and leave anything precious in the hotel safe.

The shirt is the piece to invest in, because it does the same job at home in July: TOTEME's oversized cotton-linen Garderob in sky blue, Brunello Cucinelli's soft gray linen with chest pockets, Alaïa's layered coral cotton-and-linen, The Row's fine-striped cotton Sisilia, or Oscar de la Renta's short-sleeved poplin with a floral button at the collar.

• Gray and burgundy: Brunello Cucinelli's gray linen shirt with TOTEME's burgundy silk shorts and a black one-piece.
• Coral and sand for lunch ashore: Alaïa's coral shirt with Zimmermann's sand-colored Mahon shorts and pale rubber sandals.
• Stripes and blush: The Row's striped shirt with Versace's blush cotton-and-silk shorts.

What to wear to dinner on a beach vacation

Dinner is where the destinations part ways. In San Juan, St. Thomas or the Maldives, where the evening barely cools, wear silk that moves: a printed silk twill or satin with a gathered skirt or a column that skims rather than grips. In Los Cabos, where the December night averages 57°F, and in Palm Beach, where it averages 62°F, choose a long sleeve, a knit or a covered shoulder, or bring the travel cardigan.

• A warm Caribbean night: Zimmermann's Clash Billow dress, an ivory floral silk satin with a cut-out and a knot at the waist, and gold kitten-heel thong sandals.
• Cabo: Gabriela Hearst's Ardor dress, a long-sleeved ivory knit maxi in cashmere and silk with a collar and a buttoned placket, with Khaite's red suede Loop kitten heels.
• Palm Beach: Max Mara's navy floral silk maxi, with cap sleeves and a self-tie sash, under the house's heather-gray cashmere-blend cardigan, with ivory kitten heels.
• Black for the last night: Isabel Marant's Aloise, a black stretch-silk maxi with scalloped lace at the neckline, with metallic gold sandals.

Chloé's champagne tiered maxi, in semi-sheer organic silk georgette over a lining, is for a dinner that ends with dancing, and Loewe's black silk-satin column, with a red stripe at the side, is the most formal here. Browse more designer maxi dresses.

Choose dinner shoes by the floor. On sand, any heel narrower than a wedge sinks, so wear a flat or a wedge; on a stone terrace a kitten heel is comfortable all night. Prada's silver metallic-leather wedge stands 55mm, Bottega Veneta's Riva is a 50mm kitten heel with padded straps, and Khaite's Loop is about 35mm, with an ankle strap. René Caovilla's crystal-trimmed flat thong is the pair for a party on the sand. Browse more flat sandals.

Christmas beach vacation outfits: the holiday week somewhere warm

Christmas Eve and New Year's Eve both fall on a Thursday this year. Hanukkah comes early: it begins at sundown on Friday, December 4, and ends at nightfall on Saturday, December 12, so a Hanukkah trip and a Christmas trip are two different weeks. Either way, the holiday week somewhere warm asks for clothes that read festive without velvet, wool or boots.

Christmas Eve dinner. Color does the work that velvet does at home: emerald, red and gold in silk, satin or a metallic knit. On an open terrace, Saint Laurent's one-shouldered red silk-satin minidress, ruffled from neckline to hem, carries the color; for an air-conditioned dining room, Tom Ford's long-sleeved black sequined midi is the polished alternative.

Christmas Day. Christmas lunch in the heat is the long lunch with more polish: the poplin day dress, gold sandals and gold earrings, plus a silk scarf if the day starts at church.

New Year's Eve on the sand. Choose shine that moves and breathes: lamé, metallic knit and sequins on a knit base rather than heavy beading on a lined dress. Zimmermann's Indra, a copper metallic rib-knit maxi with a knotted halter, and Alaïa's dusty-rose open-knit metallic midi are knits, and Missoni's one-shoulder mini is a light viscose lamé in a pastel chevron. Rabanne's rose-gold sequined maxi, long-sleeved and close to the body, is for a party with a floor. On the sand at midnight, go flat or barefoot. Our St. Barths guide covers New Year's Eve on the harbor in Gustavia, and our New Year's Eve outfits guide covers the night in the city.

Black tie in a warm place. One request our AI stylist received asked for an "Outfit for a black-tie party in Cabo." Our answer: a floor-length gown in metallic knit or jersey, which reads formal and stays light, a wedge in case the party moves onto the sand, and a cashmere wrap for a night in the high 50s. Oscar de la Renta's silver gown, metallic jersey fringed at the hem, and Missoni's gold halterneck maxi, crochet-knit with metallic threads and sequins, both meet that brief.

What to buy once, and what to enjoy for a season

A winter-sun wardrobe is easy to overbuy, because it is bought in a hurry for a single week. Resort, or cruise, collections, made for exactly these trips, reach stores from around mid-November, as our resort wear guide explains, so a Christmas trip can be shopped from the new deliveries while a Thanksgiving trip may have to be packed before they land. Buy once the pieces you will also wear at home:

• a solid one-piece with structure, which doubles as a bodysuit;
• a fine cashmere or cashmere-silk cardigan in ivory, gray or oat, which you will wear more in the city;
• a lined cotton poplin day dress, which goes from a Caribbean lunch to a June wedding;
• flat leather sandals with an ankle strap, and one low-heeled pair;
• one silk dinner dress in a print you would wear in July.

The one-season pleasures are the logo jelly sandals, the terry sets, the metallic minidress and the loudest print in the suitcase: enjoy them, but not at the expense of a second swimsuit.

Fit notes that save a return. Read the fit line on knits: Bottega Veneta describes its bouclé cardigan as a relaxed fit with dropped shoulders, and Max Mara its long wool-and-cashmere cardigan as a long relaxed fit, so choose your usual size rather than sizing up to layer. Poplin and linen have little or no stretch, so fit a dress to the bust and waist, which a tailor can rarely let out far. A sandal strap that marks your foot in a fitting room will rub after a day on warm stone.

The usual mistakes: pale unlined linen over a wet swimsuit, three pairs of dinner heels, and no evening layer for Cabo or Palm Beach. If you would rather start from what you already own, ask our AI stylist to plan each day of the trip from your closet and suggest only the gaps.

How we chose

• December weather first: knits for nights in the high 50s and low 60s, silk and poplin for warm ones, terry, swim fabric and rubber for showers and wet decks.
• The over-a-swimsuit test: every dress, short and top had to go on over a swimsuit and look finished at a lunch table.
• Soles for the surface: rubber with grip for pools and boats; flats, kitten heels and one wedge for dinner, and no stilettos.
• Sizes: every pick was offered in at least three sizes when we chose it in October, and most in five or more.
• Houses: 34 of them, from Pucci's prints and Missoni's knits to Loro Piana's cashmere; the Chloé pieces come from Chloé's own store.
• Price: from under $400 for jelly thong sandals to just under $8,000 for a fringed metallic gown; most of the swimwear, separates and sandals sit between about $400 and $1,000.

Frequently asked questions

What should I wear on a beach vacation in December?

Plan for warm days and variable evenings: average lows in the low to mid-70s in San Juan and St. Thomas, the low to mid-60s in Miami and Palm Beach, and the high 50s in Los Cabos. Pack swimsuits, a long-sleeved shirt, pool separates, a day dress, a dinner dress, one fine knit and flat or low-heeled sandals.

What should I pack for a Caribbean vacation?

For Caribbean or other tropical vacation outfits, pack three swimsuits, a long-sleeved linen shirt, shorts for the pool bar, a poplin day dress, a silk dinner dress, rubber sandals and a dressier pair. Nights stay in the 70s in San Juan and St. Thomas, so one light layer is enough.

What should I wear on the plane to a warm destination in winter?

Dress for arrival and add what you can carry: knit or crepe trousers or a jersey dress, a fine cashmere cardigan, a short down jacket and loafers or ballet flats, with a swimsuit and sandals in your carry-on.

What do you wear for Christmas on a beach vacation?

Use color instead of heavy fabric: emerald, red or gold in silk or a metallic knit for Christmas Eve, and a poplin day dress with gold sandals for Christmas lunch.

Is it cold at night in Cabo in December?

Cool rather than cold. Mexico's national weather service puts the December average for Los Cabos (1971–2000) at a high near 80°F and a low near 57°F, so bring a cashmere sweater or a long-sleeved dress for dinner outdoors.

What is the dress code in the Maldives?

Outside holiday resorts, including on beaches used by locals, the UK Foreign Office advises visitors to cover their shoulders, avoid short or tight shorts and keep arms and upper legs covered when bathing. Topless sunbathing is not allowed anywhere, resort islands included.

Keep reading

• Resort wear: what to pack for the beach, the harbor town, the yacht and the safari
• What to wear in St. Barths, from beach clubs to New Year's Eve
• What to wear to Art Basel Miami Beach, from fair days to beach nights
• The 25 best beach bags
• The Vacation Shop, our stylists' edit for warm-weather trips