Dad will be happy to get out of his boots and into a pair of the insanely comfortable Classic slip-ons, shown here in tumbled brown leather. He might also enjoy pairing his jeans with Roper’s Desert Stickers, which combine old-school suede style with a gum outsole and removable comfort footbed. $65 for Classics, $55 for Desert Stickers; Roper Apparel and Footwear; www.eroper.com; 888-ROPE-ONE.