“Then the opportunity to be on this boat, which I’ve admired from afar for years, came along, and I couldn’t say ‘no’. Of course, combine that with the bag …”

The bag that melted Watson’s resolve is an $85 tote made from approximately 33 plastic bottles, with $5 from every sale donated by Oroton to environmental organisation Ocean Crusaders.

The worthy sea conservation connection cruises alongside an important branding exercise, as more Australian fashion labels follow the lead of Prada and Louis Vuitton by associating themselves with sailing.

Prada chief executive Patrizio Bertelli owns the Luna Rosa Prada Pirelli sailing syndicate, which inspires the brand’s Linea Rossa range. Louis Vuitton has been associated with the America’s Cup since 1983, sponsoring this year’s event in Barcelona.

“As a brand, we’re embracing new horizons, both in design and in how we connect with our audience,” says Oroton chief executive Jenny Childs. “By sponsoring the Drumfire and collaborating with Jess Watson, we’re reinforcing our commitment to a modern Australian lifestyle that’s purposeful and deeply connected to our surroundings.

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“Both sailing and fashion revolve around precision and performance. In sailing, every knot, sail, and movement serve a purpose, much like the details in a beautifully crafted bag or garment.”

With luxury brand Rolex as the naming sponsor of the Sydney to Hobart, along with the deep pockets of Drumfire’s owner, it’s clear sailing attracts devotees with purchasing power.

Suiting label M.J. Bale – which is already the official tailor for the Australian Test Cricket team, the Wallabies, the Socceroos, the Kangaroos and the Sydney Kings basketball team – is outfitting the Unicoin crew for the race.

In a collaboration with sailmakers North Sails, M.J. Bale founder Matt Jensen has developed a capsule collection of 15 pieces combining sustainability with seafaring experience. The collection includes a jacket, a gilet, chambray shirts, French terry sweatshirts, cargo shorts, and co-branded polos and swim shorts.

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“We love sport, and so does our customer,” Jensen says. “They also love sailing.”

“I’ve had a 15-year friendship with North Sails’ creative director, Michael Sondag. We have always caught up in Italy over the years, and when he suggested working together on a new co-branded collection, I knew immediately how we could do it.”

Margie Woods, the founder of Melbourne label Viktoria & Woods, is happy to reap the benefits of sailing style without tackling the Bass Strait, preferring to apply her aesthetic to the sport’s social side with a capsule collection called Yacht Club.

Cropped blue and white tops and billowing white shorts are designed for more relaxed sailing – or a splash of rosé appreciation.

“Many Australian women are travelling over the summer months, even if it is escaping the city to Sorrento [on Victoria’s Mornington Peninsula] or the northern beaches of Sydney,” Woods says.

“I wanted to capture that balance between functionality and style – clothing that’s adaptable yet sophisticated. The modern yacht club aesthetic is evolving, fusing performance-inspired designs with a relaxed, contemporary feel that’s far removed from the dated, bourgeois Riviera vibe.”

But sailing attire – luxurious or otherwise – fails to rate a mention when it comes to when and where Watson feels most glamorous.

“It’s probably when I’m sailing at twilight and the wind is just right, and you’re feeling relaxed,” Watson says. “Who knows what you’re wearing?”

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