Make vinaigrette: Whisk together red wine vinegar, Dijon mustard, garlic and Worcestershire sauce until evenly combined.
Gradually add 1/3 cup olive oil, whisking constantly until emulsified.
Season with salt and pepper.
Meanwhile, heat remaining olive oil in a large skillet over medium-high heat.
Season chicken with garlic powder, salt and pepper and cook until cooked through, 4 per side.
Transfer to a cutting board to rest for 10 before chopping.
Toss avocado in lemon juice.
Pour 1-2 tablespoons in each mason jar.
Add tomatoes on top of the dressing, then layer the rest of the ingredients in the jar, leaving the lettuce for higher up in the jar.
Seal tightly and refrigerate for up 3-5 days.
Shake vigorously before serving to distribute dressing.