Preheat oven to 200°C (400°F). Toss bread cubes with olive oil, garlic powder, salt, and pepper until evenly coated.
Spread on a baking sheet in a single layer. Bake 12 to 15 minutes, flipping at 7 minutes, until deep golden brown and hard when tapped. Cool completely.
Mash anchovy fillets and garlic into a paste using the back of a fork in a medium bowl.
Add egg yolk, lemon juice, Dijon mustard, and Worcestershire sauce. Whisk until smooth and slightly paler in color.
While whisking constantly, pour the olive oil in a very slow, thin, steady stream until the dressing is thick and creamy.
Stir in the grated parmesan. Season carefully with salt and pepper, tasting as you go.
Place romaine in a large bowl. Add half the dressing and toss to coat every leaf. Add more dressing as needed.
Add croutons and toss gently to distribute. Top with shaved parmesan and cracked black pepper. Serve immediately.