The closest upscale, fine dining restaurant to the Short Hills Mall is The Dining Room in the Short Hills Hilton. It's been ages since we had dinner there, but the food was excellent, and I have not heard any recent reports contradicting that. The room is clubby and very comfortable. There is a second, less formal, restaurant called The Terrace.
Chatham is closer to the Mall than Summit. While the Summit exit is only a few minutes away, once you get off, you have to travel a little ways into the center of town to get to the restaurants. When you turn off to Chatham, no need to travel into the town center because Serenade and Scalini Fedeli are practically right there. S.F. is on 24 (left side of the road), and Serenade is a right turn off 24, in the Townsquare Mall.
I'm not a fan of Serenade. Considering how expensive it is, I've never had a "Wow!" experience there. The food's good but not good enough, in my view, to warrant paying such a high tariff.
i second Restaurant Serenade in Chatham. Google this and you can find their website. they have a very comprehensive site which includes directions, so you will get travel time (it is close). I have not been to Scalini Fedeli. There is also a very upscale restaurant in the Hilton at the short hills mall. I read a review about it last year and i sounded top notch. You will need reservations (hopefully not too late) i'm sure for all of these restaurants.
Okay, well givent htat you are pretty open ehre are some of my favorites. I'm from Livingston so im familiar with the area. Do yourself a favor and stay away from the Striphouse. Its not that good!
Summit: The Huntley Tavern (upscale comfort food! SO good!)
Livingston: Nero's Grill (they ahve everything...steak, seafood, great salads, etc..)
West Caldwell: Trattoria Fresco (Best italian restaurant in the area, but might be a bit far)
W. Orange: Highlawn Pavillion (Great views of Manhattan)
If i think of some others ill definitely post them!