Preheat your oven to 300°F and trim the tops of the garlic heads. Drizzle with olive oil, sprinkle salt, wrap in foil, and roast for 2 hours. Once soft and golden, let them cool before using in the dressing.
Increase the oven to 425°F and lay bacon slices evenly on a sheet pan. Roast for 20–22 minutes until crisp, then drain on paper towels and roughly chop for the salad.
In a food processor, combine lemon juice, Dijon mustard, anchovies, and ¼ cup grated parmesan. Squeeze roasted garlic into the bowl, pulse to combine, and drizzle in olive oil while processing. Season with salt and freshly cracked pepper.
Roll kale leaves lengthwise and cut into ¼” slices. Place in a large bowl with a spoonful of dressing and massage for 30 seconds. Let sit for 10 minutes to soften and absorb flavors.
Heat a skillet with olive oil over medium heat. Toast torn bread until golden on all sides, stirring often. Season lightly with salt and allow to cool slightly.
Slice romaine into ¼” pieces and add to the kale. Toss with remaining dressing for 30 seconds. Add bacon, croutons, and remaining grated parmesan, tossing gently to coat everything.
Transfer the salad to a serving platter, top with shaved parmesan, and finish with freshly cracked black pepper. Your salad is now ready to enjoy!