Bring a large pot of lightly salted water to a boil. Add penne and cook, stirring occasionally, until tender yet firm to the bite, about 11 minutes.
Meanwhile, heat 2 tablespoons olive oil in a skillet over medium-high heat. Saute pepper, onion, and garlic for 3 minutes. Add steak and Italian seasoning. Saute until steak begins to firm and is hot and slightly pink in the center, 7 to 10 minutes more. Add remaining olive oil. Drain penne and mix into the skillet.
Melt butter in a saucepan over low heat. Whisk in flour; continue cooking and stirring until a paste forms, about 2 minutes. Add evaporated milk and garlic, stirring constantly until sauce is homogenous. Add Cheddar cheese and Gouda cheese by handfuls; continue stirring until completely melted, about 5 minutes. Remove sauce from heat and drizzle over the pasta.