If there’s one thing I’ve learned over a lifetime of racing on different boats, it’s that we sailors are a needy bunch. Even if our boats are old, we eventually need new sails, we need good wet gear to keep us warm and dry, we need shoes that don’t slip on worn non-skid. We need butt pads, kneepads, and now spleen pads for long days spent creased over the lifelines. There’s all of this on top of the basic essentials: shades, hats, gloves, watches, and more. It’s a wonder we can actually leave the dock without all of it. No matter. Whatever it takes for us to race at full intensity and with full enjoyment is essential equipment. In the spirit of a holiday shopping theme, we are sharing our favorites, accessories guaranteed to make any racing sailor—big boat or small—smile, without dipping into the new-sail fund.