In a blender, puree the dressing ingredients. Transfer to a small bowl; cover and refrigerate.
Preheat the oven to 350 degrees . In a medium bowl, toss the crouton ingredients until the bread absorbs the EVOO, 1 to 2 minutes; season with salt and pepper and spread in an even layer on a baking sheet. Bake until golden and crisp, tossing once, about 15 minutes. Let cool.
In a medium bowl, mix the flour, salt and cayenne. In a medium skillet, heat 2 tbsp. EVOO over medium-high. Season 1 chicken breast with salt and pepper, then dredge in the flour mixture. Cook the chicken until golden-brown on the bottom, about 2 minutes. Turn and cook until cooked through, about 1 minute more. Transfer the chicken to a plate and repeat with the remaining EVOO, chicken and flour mixture.
In a large bowl, toss the kale, shallot and croutons with 3/4 cup of the dressing; season. (Refrigerate the remaining dressing for another use.) Divide the chicken among plates and top with the salad. Garnish with the grated Parmesan; serve with lemon wedges.