Heat a grill pan or grill to medium-high heat.
Bring steaks to room temperature, drizzle with extra-virgin olive oil and season with salt and pepper on both sides.
Place the steaks on the grill, cook meat 10 to 12 minutes for pink centers. Turn twice and let meat rest 5 minutes before slicing.
While meat cooks, brown bacon in a drizzle of extra-virgin olive oil in a medium to large skillet over medium-high heat.
Chop the leeks then soak in a large bowl of water or separate the chopped leeks by running under water. Dry the leeks in a kitchen towel.
Place cooked bacon on paper towels to drain. Pour off all but about a tablespoon of bacon drippings then add leeks and wilt down. Season cooked leeks with salt and peppe, to taste.
Transfer the cooked bacon to a food processor and add Worcestershire, vinegar, mustard, some black pepper and a splash of water. Turn processor on and stream in 1/2 cup extra-virgin olive oil.
On each dinner plate, arrange a bed of shredded romaine and thickly sliced tomatoes. Slice meat against the grain of the steak. Arrange the steak over the sliced tomatoes. Scatter the leeks over the sliced steaks and pour bacon dressing down over the top.