In a bowl, whisk the balsamic vinegar, red wine vinegar and oregano. Gradually whisk in the olive oil. Stir in the tomatoes and season with salt and pepper; let stand for 30 minutes.
Stack the lettuce leaves on 4 plates to form a flower shape, using the largest leaves on the bottom and the smallest on top. Drizzle with the dressing, distributing the tomatoes among the stacked leaves.