Preheat the oven to 375°F (190°C). Spread the cubed bread on a rimmed baking sheet. In a small bowl, whisk together olive oil, minced garlic, kosher salt, and dried oregano if using. Drizzle the oil mixture over the bread cubes and toss until evenly coated. Spread the cubes in a single layer and bake for 10–12 minutes, stirring once halfway through, until golden brown and crisp. Remove from oven and let cool on the baking sheet.

Caesar Dressing

Make dressing

In a medium bowl or measuring cup, combine the mayonnaise, finely minced anchovy fillets (or anchovy paste), minced garlic, Dijon mustard, Worcestershire sauce, lemon juice, and red wine vinegar. Whisk until smooth. While whisking constantly, slowly drizzle in the 2 tablespoons olive oil to create a slight emulsion and gloss. Season with freshly ground black pepper and salt to taste. Taste and adjust acidity with more lemon juice or sweetness with a pinch of sugar if desired. Cover and refrigerate for at least 15 minutes to let flavors meld.

Salad

Assemble salad

Right before serving: place the torn romaine lettuce in a large salad bowl. Add about half of the dressing (reserve the rest for guests to add more) — roughly 1/3 to 1/2 cup depending on how saucy you like it — and toss gently to coat the leaves evenly. Add the cooled croutons and toss lightly once more.

Finish and serve

Transfer the dressed salad to a serving platter or keep in the bowl. Sprinkle the grated Parmesan evenly over the top and finish with freshly ground black pepper to taste. Serve immediately with lemon wedges on the side and the remaining dressing passed at the table.