Cook the penne pasta according to package instructions in a large pot of salted boiling water until al dente. Drain and rinse under cold water to cool.

In a large mixing bowl, combine the cherry tomatoes, cucumber, red onion, Kalamata olives, and crumbled feta cheese.

In a small bowl, whisk together the olive oil, red wine vinegar, dried oregano, salt, and pepper.

Add the cooled pasta to the vegetable and feta mixture. Pour the dressing over the pasta and toss gently until everything is well combined.

Taste and adjust seasoning if necessary. Chill in the refrigerator for at least 30 minutes before serving to allow flavors to meld.

Serve cold or at room temperature, garnished with fresh basil leaves if desired.