Every product is carefully selected by our editors. If you buy from a link, we may earn a commission.

Kit: Racing the Rolex Big Boat Series

Offshore yacht racing may seem like a gentleman’s sport, but underestimate it at your peril. Leave the polo shirt and leather boat shoes in your shore bag for the yacht club after-party.



Image Map

Offshore yacht racing may seem like a gentleman’s sport, but underestimate it at your peril. Strong winds, big swells and lots of hard corners and sharp objects mean you’re going to get wet and beat up. So leave the polo shirt and leather boat shoes in your shore bag for the yacht club after-party. Offshore gear has become as specialized and technical as mountaineering or cycling gear, borrowing features from both while adding those specific to the rigors of jumping halyards and trimming the sails. Here’s the kit Jason Heaton used for the Rolex Big Boat Series while crewing for Escapade Racing.

MORE KITS: A Gentleman’s Golf Outing | The Perfect Day Pack | Pack Your Dopp Kitt like a Pro

Helly Hansen Skagen Jacket

Perhaps the most important piece of gear is your foul weather jacket, even though some days you might never pull it on. Full waterproof protection with breathability, in addition to bombproof (and rustproof) zippers, easy access pockets and a damn good hood are key. Helly Hansen has a lot of experience with both sailing and foul weather, having made clothing for Norwegian fisherman going back to the 19th century. The Skagen jacket is a full-on foulie with a full complement of well-placed pockets inside and out, a storm flap-covered zipper and a stowed hood, which is bright green for visibility when things go really bad; rubber seals at the wrists and a fold-over fleece-lined velcro neck closure further ensure security. Oh, and there are also reflective patches on front and back so you’re more likely to be found if you happen to go overboard in the Roaring Forties. The only issues I had were that the high collar snagged on lifelines while hiking out and the zipper was a little too finicky for quick deployment.

Buy Now: $375

Helly Hansen Crew Coastal Trousers

In San Francisco Bay, you’ll be wearing these bib pants regardless of the weather. Aside from their obvious waterproof protection, the abrasion-resistant knee and butt surfaces keep you from getting too dinged up while crawling around on deck. The well-placed single-thigh pocket was perfect for stowing gloves. Even after full days of ducking spray and a near capsize during which I was dragged chest-deep in the Bay, I came home to dry base layers. One gripe: I wished the ankle openings cinched up tighter.

Buy Now: $200

Super.natural Zipneck Baselayer

Approaching its debut on US shores, German brand Super.natural has been providing lucky Europeans with wool-blend base layers for years. The quarter-zip neck base layer is made up of a blend of merino wool, polyester and Lycra for the perfect amount of stretch, warmth while wet and no stink. On all but the windiest days, I lived in this top on its own, under my bib pants or my foul weather jacket.

Learn More: Here

Atlantis Shipyard Shorts

For more temperate racing or dock wear, the Shipyard shorts from Marblehead, Massachusetts-based brand Atlantis are perfect. The nylon fabric sheds water like Teflon and wears like iron. Buttoned cinches at the back mean you don’t have to wear a bulky belt, a gusseted crotch stretches with you and the zipped hand pocket keeps your valuables. It also contains a small side pocket, perfect for clipping a multitool.

Buy Now: $75

Maui Jim Twin Falls Sunglasses

Look around a marina and you’re bound to see a lot of Maui Jim sunglasses on skippers and crew alike. That’s because the brand has a well-earned reputation for durability and performance. The lightweight Twin Falls are made from acetate frames, built in Japan, with a screwed-on nose bridge and flexible bows. The polarized lenses cut glare well, and the slight wrapped shape stayed put through the most challenging conditions, especially when paired with Maui Jim’s clever adjustable wire keeper. Neutral gray lenses were the right choice for the mix of bright sun and overcast fog on the Bay.

Buy Now: $229

Helly Hansen 90L Duffel

All this gear needs to get to the dock, and a big duffel is just the ticket. The 90-liter Helly Hansen duffel swallowed up foulies, shoes and everything else with room to spare. The rubberized nylon tarpaulin material is weatherproof, and the zipped horseshoe opening allows easy access. Two internal mesh zip pockets work well for small stuff and hideaway backpack straps make hauling easier, though I wish they were located on the opposite side so the had straps and zipper didn’t ride against my back.

Buy Now: $120

Spinlock Deckvest Lite

Racing life vests are different than those you wear on the family pontoon boat. The Spinlock Deckvest Lite is the gold standard of offshore racing wear: it has a sensor that self-inflates the vest when flooded with water, keeping it unobtrusive and streamlined until you need it. A crotch strap keeps the vest from riding up around your head should you go in the water. Multiple attachment points for beacons, lights or a spray hood round out the features.

Buy Now: $189

Spinlock Kneepads

Aside from gloves (see below) the most important piece of kit during the Big Boat series was my kneepads. Especially on the foredeck, you’ll spend a lot of time on your knees, crawling around during tacks and rigging sails on the fly. Kneepads aren’t rocket science but these Spinlocks are designed for sailors who will be wearing them under foul weather bibs so they’re minimalist and breathable.

Buy Now: $45

Harken Reflex Gloves

Jumping halyards is murder on the hands. Wet lines are slippery, which not only makes gripping them difficult but can also cause killer rope burn. These fingerless Harkens use a proprietary palm material called Black Magic that is grippy even when wet and the gloves dry quickly and won’t stretch out. Though they’re durable, you’ll be lucky to get a full season out of a pair, so buy two.

Buy Now: $35

Zhik Deck Beaters

A piece of kit I wish I’d worn, these Zhik tights were essential gear for Escapade’s intrepid bowman as he scrambled around the foredeck. The padded seat and knees provided much-needed cushioning and some warmth even when worn only under a pair of shorts and prevented countless bruises in the process. Or so I’m told.

Learn More: Here

Rolex Submariner

While some would argue that wearing a luxury timepiece on board a racing yacht is nothing short of insane, there’s no denying the Submariner’s legacy among countless skippers, both as a trusted companion and motivation — the winners of the Big Boat Series get one. I wore my old Sub on a nylon NATO strap through brutal race conditions, and though the bezel got snagged and popped off during a hoist, the watch continued to keep chronometer-spec time. The modern Submariner features a scratchproof ceramic bezel and Parachrom hairspring for resistance to magnetic influence, in addition to the stainless steel case’s 300 meters of water immunity. The Submariner may be expensive, but a Rolex is one of the soundest investments you can make, durable enough to last a few generations and often increasing in value along the way (assuming you don’t lose it in the Bay).

Learn More: Here

Advertisement - Continue Reading Below
More From Accessories