Sailing Core: Historic vs Modern

Sailing Core: Historic vs Modern

The striped shirt was a French Navy regulation. The blazer was a captain scrambling to impress a queen. The trousers flared at the ankle so a drowning man could kick them off and use them as a flotation device. The shoes were carved with a penknife by a guy staring at his dog's paws. Every single piece of clothing that now reads as effortless coastal elegance started its life as gear for men who were, at some point, extremely worried about staying alive on the water.

The Clubs That Started It

Yacht racing was born off Cowes, on England's Isle of Wight. The Royal Yacht Squadron formed in 1815, and by 1826 they were racing for a hundred-pound cup. That regatta grew into Cowes Week, which still runs every August and marks its 200th anniversary in 2026. Around the same time, the British aristocracy discovered the French Riviera as a winter escape. Lord Brougham got stuck in Cannes during a quarantine in 1834, fell in love with the place, and built a villa. By the 1880s American millionaires were cruising the Côte d'Azur in yachts of their own.

Across the Atlantic, Newport, Rhode Island became the American answer. The New York Yacht Club held its first regatta there in 1883, and Newport hosted the America's Cup for fifty-three straight years until the United States finally lost it in 1983, breaking the longest winning streak in the history of organized sport. This is where American nautical prep grew its roots, and it never fully let go.

The Breton Stripe

On March 27, 1858, the French Navy issued a regulation that made a striped knit shirt official uniform for sailors based in Brittany. The specifications were exact: 21 white stripes, each twice as wide as the 20 or 21 indigo blue stripes running between them. The stripes made a man easier to spot in the water if he went overboard. Function first, always.

Coco Chanel found the shirt on the fishermen along the Normandy coast and put it on wealthy women in 1913, then locked it into her collections by 1917. It was the first time genuine workwear had crossed straight into high fashion, and it landed like a bomb on a corseted era. Picasso wore one. So did Brigitte Bardot. Jean Paul Gaultier called it his identity card, the pattern that goes with everything and never goes out of style. It has not.

The Navy Blazer

The story, whether entirely true or slightly polished, goes that in 1837 a British captain learned Queen Victoria would inspect his ship and panicked at the state of his crew's uniforms. He outfitted them in short navy jackets with brass buttons overnight. The Queen was impressed. The style took the ship's name and never let go, migrating from the deck to the rowing club to the yacht club, where crested brass buttons became a wearable membership card for anyone who knew how to read them.

If you want the modern version of that same signal, a well-cut jacket from San Martini's Jackets and Blazers collection does the same quiet work a hundred and ninety years later.

The Boat Shoe

In 1935, a sailor named Paul Sperry slipped off a wet deck one too many times and decided to fix the problem himself. Watching his cocker spaniel bound across the ice without slipping, he examined the dog's paw and noticed a network of fine grooves. He took a penknife to a rubber sole and carved a similar pattern, a technique called siping that channels water away and grips a wet surface. His first shoe sold by direct mail to sailing clubs in 1935. In 1940 it became official U.S. Navy footwear. It remains the official shoe of the America's Cup today, worn without socks, brown leather against a white non-marking sole, the single most recognizable object in the entire nautical vocabulary.

Wool Knits and the Fisherman's Sweater

Long before performance fabric existed, there was grease and wool. Fishermen's wives across the British Isles knitted tight, dark sweaters called ganseys, named for the island of Guernsey, dense enough to block wind and shed water. Ireland's Aran sweater grew from the same tradition, using cream-colored wool with the natural lanolin left in for water resistance, the cable and diamond stitches trapping warm air against the body. After Vogue featured the fisherman sweater in the 1950s, everyone from Grace Kelly to Steve McQueen was photographed in one. On a boat, wool still does its old job of regulating temperature over cold water. On land, it just reads as heritage.

For that exact warmth-with-history feeling on a cool evening, San Martini's Sweater Weather collection carries the crewneck knits built for the same layering logic sailors figured out generations ago: light enough for a boat deck at dusk, warm enough for a walk home after.

The Polo Shirt

Not everything nautical came off a boat, but it lives in the same clubhouse world regardless. French tennis champion René Lacoste got tired of stiff long-sleeved shirts and designed a short-sleeved piqué cotton shirt with a soft collar, debuting it at the 1926 U.S. Open, which he won wearing it. He embroidered a crocodile on the chest, founded La Chemise Lacoste in 1933, and accidentally created the uniform of every yacht club, golf course, and seaside terrace for the next century.

The Captain's Cap

The peaked mariner's cap started as cheap, practical workwear early in the 1800s. The version with gold braid and a white top became the mark of a yacht's skipper, a small piece of hierarchy readable from across a marina. On a modern charter deck it is still half function, half theater, and entirely recognizable. However, in modern times we've traded the captains hat for a Dad Hat; as the cap is easily worn, fits comfortably, and is multi-purpose on and off the boat. 

Modern Era, Part One: The Technical Revolution

Here is a detail that reframes the whole story. As late as the 1964 Tokyo Olympics, competitive sailors were still racing in flannel trousers and wool Guernsey sweaters. British sailor Keith Musto, who won silver that year, put it plainly: they sailed in old wool and flannel for years, got wet, and simply accepted it. He decided that was ridiculous and founded a technical sailing brand the same year to build proper waterproof, breathable gear.

That decision split nautical clothing in two. Serious sailors today wear systems, not outfits. A synthetic or merino base layer wicks moisture. A fleece mid-layer insulates without soaking through. A waterproof-breathable shell keeps spray out while letting sweat escape. The rule drilled into every modern sailor is simple: avoid cotton, because wet cotton holds moisture and steals body heat fast. This branch of nautical style has almost nothing to do with looking nautical. It is pure function, exactly the way the original Breton stripe and sailor trouser once were.

Modern Era, Part Two: Quiet Luxury on the Water

The other branch went the opposite direction entirely, chasing pure aesthetics. Quiet luxury, understated, logo-free, built from natural fiber in muted tones of navy, cream, and sand, found its natural summer expression in nautical dressing. The Amalfi Coast, Portofino, and St. Tropez run on a linen-first uniform where the palette matches the coastline itself: white, sand, navy, ocean blue, worn with a fit that looks relaxed but was clearly chosen with care.

Linen deserves credit here beyond just looking good in the heat. It was the original fiber of sails themselves, before cotton and then synthetic fabric took over in the nineteenth and twentieth centuries. The same fiber that once caught the wind now catches the eye on every coastal terrace from Capri to Cannes, and for good reason: it breathes, it moves, it works in heat that would flatten heavier fabric.

For that exact linen-first version of the aesthetic, San Martini's French Riviera collection and the Weekend Resort Trip edit both draw from the same coastal logic: breathable, natural, built for a climate rather than a costume. And no coastal look is finished without the right hat. Whether it is a captain's cap or a wide-brim straw for the deck at noon, the Hats collection covers both registers.

Where the Two Meet: Monaco & Beyond

At the very top of the market sits the Monaco Yacht Show, held every September at Port Hercule since 1991, drawing tens of thousands of visitors to an in-water fleet of superyachts averaging well over a hundred feet. The dress code there is officially "business casual or nautical chic," meaning Riviera linen by day and something considerably dressier by night. Even the most seasoned yacht-hopping style guides still recommend original leather boat shoes for the deck, proof that the 1935 invention has never actually gone out of use. The clothes came full circle: born on working boats, refined into fashion, and now worn again on boats, just considerably larger ones.

This Works Year Round For Travel

The whole point of nautical style, historic or modern, is that it was built for movement. Natural fibers that breathe in heat and layer in cold. A palette of navy, white, cream, and sand that never clashes with itself, no matter how you mix it. Pieces designed to survive salt air, sun, and long days, which means they survive airports and long flights just as easily.

Build the capsule once. A striped shirt. A blazer that fits properly. Well-cut trousers. Real leather boat shoes worn without socks. One good wool knit for cool evenings. A linen shirt for the heat. One reliable hat. That collection of seven pieces will get you through a weekend in Newport, a week on the Amalfi Coast, and a random Tuesday at home with equal ease, because none of it was ever really about the boat. It was about dressing for a life that moves, which, if you travel with any regularity at all, is exactly the life you are already living.

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