Sensible optionHerschel Supply x Stussy, $88 
Splurge optionBillykirk, $350 
Why dad needs it: You probably can't afford to give your dad a weekend vacay, so give him the means to take more trips when his hard-earned time off comes around. Whether he takes a few days to chill out of town with his homies, or spend a romantic weekend with his lady, get him something he can haul his gear in style, instead of that raggedy bag that's leftover from his vagabond days.