For the dinghy sailing dad, the best footwear you can hook him up with is a pair of Sperry Top-Sider’s GripX3 Seahiker, developed with input from the Olympic sailing athletes of Team Sperry Top-Sider. These neoprene boots have everything going for them: a rubberized “Top Deck 360” to pad and grip a hiking strap, STS’s patented “Son-R Technology” sole, which will activate pressure points on the bottom of his feet (allowing him to “see his feet”), and vent holes to allow water to drain. The side-zip makes them easy to get on and off, and the curved zipper keeps the boot streamlined and snug. I'm six months into one pair with heavy use and they’re holding together great, and still smelling fresh. $80 www.sperrytopsider.com -Dave Reed