In a medium mixing bowl, whisk together mayonnaise, sour cream, white wine vinegar, sugar, Dijon mustard, and Worcestershire sauce. Season with salt and black pepper to taste, whisk until smooth.

Bring a large pot of salted water to a boil and cook macaroni pasta according to package instructions until al dente, about 8–10 minutes. Drain and rinse under cold water.

Finely chop romaine lettuce, dice red bell pepper, finely dice red onion, chop celery, and thaw green peas if using frozen. Organize ingredients in bowls.

In a large trifle bowl, layer chopped romaine lettuce, cooled macaroni, diced red bell pepper, red onion, green peas, chopped celery, diced ham, and chopped black olives.

Pour dressing evenly over all layers and top with shredded cheddar cheese.

Cover salad tightly and chill in the refrigerator for at least 5 hours, preferably overnight.

Before serving, gently toss layers to mix dressing. Serve chilled.