I knew it was time to replace my beloved Dubarry Ultima sea boots when, after 12 years, the sole started peeling off. Trouble was, it unfurled during a wet and cold race on Puget Sound in March. But, being a cheap Yankee, I spent the next year rehabilitating them with Shoe Goo (not the manufacturer’s recommended fix), each time with diminishing ­marginal returns. Finally, I broke down and went to my local chandlery. Decades of every-­other-day running turned my feet into embarrassing-­looking paddles, and while brand loyalty guided me toward a new pair of Dubarry Ultimas, the salesman instead recommended a ­beamier-looking pair of Musto Gore-Tex race boots. While I was initially skeptical, my Hobbit-like feet felt warm and happy in the showroom.

Forty-eight hours later, I sea-trialed my new nautical armor during an early January blustery sail. Air temps hovered in the mid-30s, but my feet stayed warm and dry, as did the rest of me. Lesson learned? While frugality has its merits, having the right boots, gloves and hats is critical if you’re foolhardy enough to sail on days when smarter people go skiing. Here’s a look at cold-weather kit to help you stretch your sailing season.

Head Heaters

Depending on conditions, hats often need to serve double duty by providing warmth and sun protection. Gill’s OS waterproof hat accomplishes these jobs while offering waterproof protection. The fleece-lined hat features a sun-cutting visor with a wired peak, ear flaps and seam-sealed construction. You can adjust the hat’s volume using a pull adjustment, and the hat’s chin strap is conveniently removable.

Baseball caps work great in the summer, but shoulder-season and winter sailing usually demand more warmth. Musto’s fleece-lined waterproof cap employs a heat-retaining fleece lining and fold-down flaps for trapping body heat from the back of your neck and ears. A peaked visor stands ready to shade your eyes on sunny days while also providing drizzle or snow protection.

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