Place potatoes in a pot, cover with cold water, add salt, and boil until fork-tender (12–15 minutes).
Pat ribeye dry and season all over with salt, pepper, and Italian seasoning. Let sit at room temp while onions cook.
In a skillet over medium heat, cook onion in olive oil and 1 tbsp butter with a pinch of salt. Stir often for 10–15 minutes. Add garlic and cook another 30–60 seconds. Push aside or transfer to bowl.
Raise heat to medium-high. Add 1 tbsp butter. Sear ribeye 3–5 minutes per side until your preferred doneness (130°F for medium-rare). Add Worcestershire sauce at the end if using.
Transfer steak to a plate, loosely tent with foil, and rest for 8–10 minutes.
Drain potatoes. Return to pot and mash with butter, cream, sour cream, garlic, salt, and pepper until smooth and fluffy. Add more cream if needed.
Return onions to the skillet. Stir in pan juices. Add a splash of broth or butter if pan is dry. Keep warm.
Slice rested steak against the grain. Plate mashed potatoes, top with steak, spoon over caramelized onions and pan juices. Garnish and serve immediately.