Turn on oven to 425°F. Bring a pot of salted water to a boil. Once the water is boiling, add the macaroni and reduce heat to simmer. Cook for 5-7 minutes or until el dente. Drain and set aside.
Toss the butternut squash with a drizzle of oil, and season with salt and pepper. Spread out in a single layer on the baking sheet and place in the oven. Set a timer for 20 minutes.
Heat an oven safe skillet over medium-low with 1 tbsp. of butter or oil (2 tbsp. for 4 servings). Add onion and cook, stirring occasionally for 15 minutes or until onions are very soft and slightly golden. Add garlic and kale to the skillet and cook until kale is bright green, about 2 minutes. Remove vegetables from skillet and set aside.
Melt 1 tbsp. of butter or oil (2 tbsp. for 4 servings) in the used skillet. Once melted, add flour and a pinch of salt. Whisk together to form a smooth paste, then slowly whisk in 2 cups of milk (4 cups for 4 servings) a little bit at a time. Return the skillet to medium heat and cook the sauce for 3-5 minutes until it has thickened. Stir in the aged white cheddar cheese.
Once timer for butternut squash goes off, add into the oven safe skillet along with cooked pasta and kale and garlic mixture. Toss everything together to coat with sauce. Layer asiago cheese, parmesan and panko breadcrumbs on top of the mac and cheese. Set oven to broil and place skillet on top rack for 3-5 minutes, or until cheese is melted and bubbly. Divide between serving dishes and enjoy!