What side dishes and dessert to serve with Italian meatloaf ?
IMO meatloaf goes best with potatoes. However, you've made Italian meatloaf, and I don't believe it should be served in the usual way a la American style meatloaf (with mashed potatoes or similar), because that doesn't support an Italian theme for the meal. The use of pasta seems logical but pasta does not appeal to me as an accompaniment to meatloaf. IMO meatloaf goes best with potatoes.
But what kind of potatoes? IMO the answer is of course Italian style potatoes. I Googled up some recipes and picked those that looked appealing to me. Not knowing what is in your Italian style meatloaf I'm assuming it has an Italian style tomato sauce. I would not want to have a tomato sauce meatloaf have its flavors duplicated in a potato side dish so I've ruled out tomato-y recipes and here's what's left:
Basic recipes:
Rachael Ray's Official Website - Italian-Style Skillet Potatoes
Italian Style Roasted Potatoes Recipe - Food.com - 46525
These two are a bit more complicated:
Roasted Sicilian Potatoes
Roasted Italian-style potatoes from Mike's Table
They all involve potatoes of course, and usually EVOO, Kosher salt, garlic, rosemary, one or more cheeses (Parmesan, Romano), sometimes other herbs (oregano, Italian parsley, thyme) and perhaps some pepper flakes. Some include additional ingredients such as olives, raisins, bell pepper, spinach leaves, cherry tomatoes... (I don't think the tomatoes as a minor ingredient would compete with the tomato-y meatloaf, but could be left out).
So I haven't cooked any of these but they all look good whether served with Italian meatloaf or with some other main dish. In fact they looked good enough that I bookmarked some of them for trial at a later date.
So my advice is to accompany your Italian style meatloaf with a non-tomato Italian style roasted or skillet potato dish.