Remove steaks from fridge and allow to come to room temperature, about 20 minutes before cooking.
Preheat oven to 350 degrees. Place cast iron skillet (or other oven-safe skillet) on stove top and preheat over medium to medium-high heat. Add olive oil to pan if skillet is dry or not properly seasoned. Swirl to evenly coat bottom of pan.
Season steaks with salt and pepper evenly over all sides of the steak.
Place steaks into preheated skillet and sear for 2-3 minutes on each side, until a golden crust begins to form and the steaks easily release from the pan. Turn over and repeat on other side of steak. Once steaks have been seared on both sides, carefully place skillet into the pre-heated oven.
Bake for 8-12 minutes, depending on the thickness and desired “doneness” of your steak. For a 2-inch Thick Cut New York Steak 10 minutes came to 145 degrees or medium rare.
Remove carefully from oven using hot mitts. Tent lightly with foil and allow the steaks to rest for 8-10 minutes, allowing the juice to redistribute into the meat. Serve immediately.