Hamilton Khaki Pioneer Handwinding Field Watch

Hamilton built watches for the armed forces in both world wars; they're now much sought-after classics. More reliable and easier to find: the Pioneer, which recalls 1940s military watches, with its semimatte bezel and leather cuff. If you'd like to go full-on retro, wear it with its protective leather flap (not necessary to prevent scratching). [$795; hamiltonwatch.com]