Bring a large pot of salted water to a rolling boil. Add rigatoni and cook according to package directions for 10-12 minutes until al dente. Drain and rinse under cold water. Set aside in a large mixing bowl.

In a medium bowl, whisk together olive oil, red wine vinegar, Dijon mustard, minced garlic, salt, and pepper until well combined. Set aside.

Heat 2 tablespoons of olive oil in a skillet over medium-high heat. Season chicken breast with Italian seasoning, salt, and pepper. Sear chicken for about 8 minutes on one side. Flip and cook until the internal temperature reaches 165°F, about 8 more minutes. Let rest for 10 minutes before slicing.

In the large bowl with the cooled pasta, add halved tomatoes, sliced roasted red peppers, halved olives, and capers. Add chopped chicken and drizzle with the vinaigrette. Gently toss until combined.

Sprinkle Parmesan cheese over the salad and add arugula, chopped basil, and fresh oregano. Toss lightly to combine.

Chill in the refrigerator for at least 30 minutes before serving to allow flavors to meld.