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Step 1
Preheat oven to 425°. Tear ½ small loaf country-style bread into bite-size pieces (you should have about 5 cups). Toss on a rimmed baking sheet with 3 Tbsp. olive oil; season with kosher salt and freshly ground black pepper. Bake, tossing halfway through, until golden brown and crisp, 14–16 minutes. Let croutons cool.
Step 2
Meanwhile, shave 2 oz. Fontina or provolone cheese with a vegetable peeler or thinly slice into strips. Finely chop 1 cup pitted Kalamata olives and ½ cup drained Peppadew peppers in brine.
Step 3
Toss Fontina cheese, olives, Peppadew peppers, 1 very small head of iceberg lettuce, thinly sliced, ½ medium red onion, thinly sliced, 1 pint cherry tomatoes, halved, quartered if large, 10 oz. pearl mozzarella, drained, 7 oz. sliced deli ham, thinly sliced into strips, 4 oz. sliced salami, thinly sliced into strips, and croutons in a large bowl to combine. Drizzle 3 Tbsp. red wine vinegar and remaining 3 Tbsp. olive oil over, then add 1 tsp. dried oregano and season with salt and black pepper. Toss again to coat. Taste salad and add more oregano if needed.
Step 4
Divide salad among plates and season with more pepper.