Heat the oil in a large saucepan over medium heat. Add the garlic and cook until golden but not browned, about 1 minute. Add the tomatoes and their juices, red pepper, oregano, salt, and sugar. Bring to a boil. Reduce heat to medium-low and simmer (crushing the tomatoes with the back of a wooden spoon if using whole tomatoes) until the sauce thickens slightly, about 20 minutes. Remove from heat. Add the olives, basil, and Feta and toss.
Cook the penne according to the package directions. Drain and divide among individual plates. Spoon the sauce over the top.