Warm oil in a large skillet over medium heat. Add garlic and cook until fragrant, about 1 minute. Stir in tomatoes, crushed red pepper and olives, and simmer until mixture is thickened, about 10 minutes.
Add shrimp and cook, stirring, until shrimp are pink and firm, 4 to 5 minutes.
Divide shrimp and tomatoes among 4 plates. Sprinkle each with feta cheese and oregano and serve hot.