Resortwear: Year Round Staples

Resortwear: Year Round Staples

A century ago, resortwear solved one very specific problem: what does a wealthy woman wear on a steamship in January when her entire closet is built for a winter she is actively fleeing?

The answer changed fashion forever. It also, quietly, gave the rest of us permission to stop dressing for the season on the calendar and start dressing for the life we are actually living. If you travel often, or simply want to feel like you are somewhere warm and unhurried even when you are standing in your own kitchen in February, resortwear is not a summer indulgence. It is the smartest wardrobe strategy you are not using yet.

The Trip That Started It All

In 1919, Coco Chanel noticed something. Her wealthiest clients were taking mid-winter holidays to warm places, and their closets, stuffed with wool and fur for a Paris December, had nothing appropriate to offer them. So she built a small collection specifically for the journey. Light. Easy. Made for a steamship deck rather than a drawing room. It is widely credited as the first true resort, or cruise, collection, and it opened a door that has never closed since.

The category grew fast because the world it served grew fast. Wealthy travelers in the early twentieth century did not take quick trips. They left for months, chasing warm weather across the Mediterranean, the Caribbean, Palm Beach, Monte Carlo. Deck luncheons. Port excursions. Evening cocktails on a terrace somewhere the sun had not yet decided to set. None of that could be dressed for with a standard seasonal wardrobe, so an entirely new category was born to fill the gap.

Then air travel did what air travel does. It made the sun reachable for everyone, not just the people who could afford a private railcar. Resort stopped being a niche indulgence for the very few and became one of the most commercially important seasons in the fashion calendar, sitting quietly between fall and spring, arriving in stores each November when the coats have already started to feel a little too familiar.

Quiet Over Loud

Here is where resortwear splits into two very different roads, and only one of them is worth walking.

Road one is the loud vacation costume. Neon prints. Logos the size of dinner plates. Clothes that announce, at volume, that you are On Vacation, as though the point of getting away were to be recognized rather than to actually rest.

Road two is quieter. It favors natural fibers, muted color, and craftsmanship over branding, and it does not need to shout because it already knows what it is.

That second road is where San Martini lives, and it is where the smart money in fashion has been moving for several years now. Quiet luxury has become one of the defining shifts in how people dress, not because it is trendy to look understated, but because it is genuinely more useful. A beige linen shirt that fits correctly does more work in a real life than ten printed shirts that only work on one specific beach.

The Pieces That Refuse to Retire

The garments that make up a true resort wardrobe were, almost without exception, never designed to be precious. They were designed to work. That is exactly why, decades or centuries later, they still do.

Linen is the oldest one here by a spectacular margin. Archaeological evidence traces flax fiber use back tens of thousands of years, and by the time of ancient Egypt, linen was not just clothing. It was currency, sacred cloth, the wrapping for the dead. Egyptians loved it for the same reason you will: it stays cool against the skin in real heat. But here is the part most people miss entirely. Linen is not a one-season fabric. Its fibers are hollow and slightly thicker than cotton, creating a natural network that regulates temperature in both directions, pulling heat away from the body in summer and helping retain warmth when layered underneath something heavier in winter. A linen shirt earns its keep in July on a boat and again in November under a sweater on a cold flight. Two seasons, one shirt, zero waste.

The crewneck sweater started its life on an athletic field, not a runway. The name traces to sweaters worn by rowing crews, and the crewneck T-shirt itself was developed in the 1930s as an undergarment meant to absorb sweat and keep football shoulder pads from chafing. A lightweight crewneck knit today does exactly what it always did: it works alone on a cool evening and layers instantly over a linen shirt the moment the temperature drops. It is the single most transitional piece a traveler can own.

The Johnny collar shirt, also called a grandad or banded collar, traces its roots to British military uniforms from the First World War, where a simple banded collar replaced the more formal styles of the era. It found its way into fashion in the 1950s, helped along considerably by a certain Indian prime minister's fondness for muslin banded collars in warm climates, which is why you will sometimes hear the style called a Nehru collar. The whole appeal is right there in the shape. No tie required. Open at the neck, breathable, equally correct at a beach lunch and a dinner table. It solves the exact problem a traveler faces every single day: dressing once, for everywhere the day might lead.

Sweatshorts, in their elevated, tailored form, descend from a longer and stranger lineage than you would guess. The modern short was effectively born on Bermuda during the First World War, when British soldiers adapted their uniforms to the subtropical heat, and Bermuda shorts crossed to America in the 1920s and 30s as a marker of travel and leisure. Today's soft cotton or French terry sweatshort, worn with a crewneck and clean shoes, is off-duty style at its most honest. Comfortable enough for a flight, sharp enough that nobody mistakes it for pajamas.

Woven knit sweaters for the beach and the boat owe everything to the Breton fishermen of the North Atlantic, who needed a garment tight enough to resist the wind and wide at the neck so they could pull it on and off quickly with wet hands. That functional origin is exactly why a lightweight version works so well today as a beach cover-up or a layer for the ride back to the marina once the sun starts to drop and the water gets a little sharper on bare skin.

Building the Actual Wardrobe

The good news is you do not need very much of this. You need the right pieces, chosen once, worn constantly.

Start with the spine: two linen shirts and one pair of linen trousers in a neutral color, because linen is the single most versatile fabric on this entire list and everything else should be built to talk to it. Add a lightweight crewneck for layering, one Johnny collar shirt for the nights that need slightly more polish without requiring a tie, one pair of elevated sweatshorts for the days that are genuinely off duty, and one nautical knit for the boat, the beach, or the walk back from either.

The full range of exactly these pieces lives in San Martini's Weekend Resort Trip collection, curated specifically for travelers who want a wardrobe that works everywhere rather than a suitcase full of single-use outfits.

The math behind this approach is simple and genuinely persuasive. Cost per wear divides a garment's price by how many times you actually wear it. A well-made linen shirt worn eighty times across four seasons costs pennies per wear. A trendy print shirt worn twice before it feels dated or falls apart costs considerably more, even at a fraction of the price tag. The expensive piece, chosen correctly, is very often the cheap one in the end.

There is a waste argument here too, and it is worth sitting with for a moment. Research from the Ellen MacArthur Foundation found that the average garment gets worn dramatically fewer times today than it did fifteen years prior, and the average closet holds dozens of pieces that have not been worn in the past year at all. Buying fewer, better resort pieces made from natural fibers is not just a style preference. It is the antidote to a genuinely wasteful cycle.

Bringing the Resort Home

Clothing is half the equation. The other half is what is in your glass.

A resort cocktail has a specific job that a regular cocktail does not: it needs to be light, refreshing, and built for an afternoon that has no particular interest in ending. Learn a handful of these and you can summon a coastline from your own kitchen table in the middle of January.

The Aperol Spritz was born in Padua in 1919, the same year Chanel built that first resort collection, created by two brothers after years of experimenting with the bitter orange liqueur. Built simply over ice with Prosecco and a splash of soda, it remains, as one writer put it, an Italian sunset compressed into a glass.

Pimm's Cup dates back to a London oyster bar owner named James Pimm, who created his gin-based tonic sometime in the 1820s or 30s as a digestive aid served in a small tankard. Loaded today with cucumber, mint, and fruit over ice, it has been the taste of English summer, and specifically of Wimbledon, since a Pimm's bar first opened at the tournament grounds in 1971.

Rum punch is the oldest formula of the group, remembered by a rhyme every bartender in the Caribbean still knows by heart: one part sour, two parts sweet, three parts strong, four parts weak, finished with grated nutmeg. It carries a complicated colonial history worth acknowledging honestly, but the drink itself, built correctly, remains one of the most genuinely satisfying things you can pour on a warm evening.

The Dark and Stormy comes from Bermuda, reportedly mixed by British officers just after the First World War using the local dark rum and the ginger beer that was already sitting behind every bar on the island. And the Painkiller, the unofficial national drink of the British Virgin Islands, was created in the early 1970s at a tiny beach bar so remote there was no dock, meaning every visitor had to swim ashore and dry their money out on the sand before they could order one.

None of these drinks require much. What they do require is the right glass, and this is the detail people skip that actually makes the difference. A tall Collins or highball glass keeps a fizzy drink lively longer, because the narrow shape reduces the surface area where carbonation can escape. A proper coupe, broad and shallow with a long stem, keeps your hand's warmth away from the drink and has done exactly that job since the seventeenth century. Cold matters more than people think. Soda water chilled properly holds significantly more carbonation than soda water served lukewarm, which is the entire reason a well-stocked home bar keeps its glassware in the freezer rather than the cupboard.

The Only Real Rule

None of this requires a passport. It requires a linen shirt that fits, a sweater you actually reach for, and a cold drink poured into the right glass on an ordinary weekday.

That is the whole promise resortwear has been making since 1919, and it still holds. You do not need to be somewhere warm to dress and drink like you are. You need the right pieces, chosen once, worn consistently, and the good sense to stop treating them like a costume for two weeks a year.

Build the wardrobe. Pour the drink. See how much of the year suddenly feels like vacation. Enjoy the food and the company with friends. Cheers!

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