Marinate steak with olive oil, juice of 1 lemon and 2 teaspoons honey. Season with salt and pepper. Let rest for 10 minutes.
On medium high heat, sear the steak for 5 minutes of each side.
Take steak out of the skillet and let it rest.
Meanwhile make the vinaigrette by combining in a small bowl the red wine, 1 cup olive oil, dijon mustard, 2 teaspoons honey, Worcestershire sauce, 3 tablespoons lemon juice, and seasoning it with salt and pepper. Whisk everything together.
In large individual salad bowls, arrange tossed arugula with chopped tomatoes.
Cut skirt steak at an angle against the grain. Arrange on top of salad.