Trim the top of the fennel and save the leafy greens for the dressing. Peel the outside of the fennel bulb if it appears to be tough or is discoloured. Core the bulb and then halve and thinly slice.
Place the vinegar, orange juice, oil, chopped fennel leaves, salt and pepper in a large bowl and whisk to combine. Add the sliced fennel, tomatoes and oranges and gently toss to combine. Let the flavours meld for 20 minutes, then gently toss again before serving.
Recipe Options: When beefsteak tomatoes are unavailable, replace them with 5 to 8 on-the-vine, plum or campari tomatoes. For additional flavour and visual appeal, include 1/2 cup of nicoise olives in the mix of ingredients used to make this salad. Give the salad a fresh herb flavour by tossing in 2 Tbsp. each of chopped fresh mint and basil.