Toast the bread and make the dressing a day ahead. Cut all the greens up to a day ahead, an store in an airtight container in the fridge.
- Heat oven to 350°F. Toss bread with 2 Tbs. oil in large bowl, then transfer to baking sheet. Bake 20 to 25 minutes, stirring occasionally, or until golden.
- Place vinegar and shallot in small bowl, and season with salt and pepper, if desired. Whisk in remaining 1/3 cup oil.
- Combine radicchio and kale in large bowl. Add 6 Tbs. dressing, toss well, then gently massage greens to slightly wilt them. Add endives, dates, and croutons, and gently toss to combine. Offer extra vinaigrette at the table.