Preheat the oven to 375 degrees F. On a cutting board, season each pork chop with 1 teaspoon Italian seasoning, ¾ teaspoon black pepper, ¼ teaspoon red pepper flakes.
In a 12-inch oven safe skillet, heat 1 tablespoon olive oil over medium-high heat. Sear each side of pork chop until golden brown, about 1-2 minutes per side. Remove from pan to cutting board.
Add onion and 1 tablespoon olive oil to the skillet. Sauté onion until fragrant and turning translucent. Add 3 teaspoon minced garlic and bell peppers, stir to combine and sauté 10 minutes until softened. Add crushed tomatoes and stir to combine.
Bring to a simmer, add pork back to center of skillet and baste pork with tomato sauce. Remove skillet from heat.
Starting from the outer edge of the skillet, alternate sliced eggplant, tomato, squash and zucchini arranged on top of sauce. Repeat pattern working from edge to center of skillet around pork chops.
In a small bowl, whisk together remaining olive oil with remaining garlic, basil, parsley and thyme. Season with salt and pepper if desired. Drizzle herb dressing over vegetables and cover the skillet with foil.
Bake for 25-30 minutes or until veggies are fork tender. Remove foil and switch oven to broil on high for 3-5 minutes, or until veggies begin to brown and pork has reached an internal temperature of 145 degrees F. Using oven mitts, remove skillet from oven and let rest 3 minutes before serving hot.
