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, sugar, and ½ teaspoon salt. Bring to a boil.
Reduce heat to medium-low. Simmer (crushing the whole tomatoes, if using, with the back of a wooden spoon) until the sauce thickens slightly, about 20 minutes.
Meanwhile, cook the penne according to the package directions. Drain and divide among plates.
Add the olives, basil, and Feta to the sauce and toss. Spoon over the penne.