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Slice the large-to-medium tomatoes and halve the smallest. Pick the leaves from the herbs and roughly chop, then mix the herbs with the shallots.
Choose a large platter and start layering up the tomatoes, mixing colours and sizes. As you finish each layer, scatter with some of the herb-shallot mix and some ground black pepper. Keep layering until everything is used up. Cover and chill for a few hrs. Bring to room temperature 45 mins before serving.
Whisk together the dressing ingredients with some salt, then drizzle over the salad and serve.