Doesn't look like an 88 to me. I have an 85 SS, those tail lights are pre 87, and the mirrors look like the 'bullet' style not the sport style. Both look like what I have on my 85, so I would say 85 or earlier?
I saw wiring for the third brake light but I didn't see the defrost grid dedicated to it hard to tell though that's why I said 85 I added a third brake light to my 83 so the wiring is not that hard to do
Looks like factory wiring poking up for a 3rd brake light through the package tray. Factory t-tops, could be 85-88, doors often swapped due to rust. Will guess 86’ due to the brake light and rear bumper/tails (would be odd for a 87-88 to be converted to the earlier style) but yea, who knows with so many variables and almost nothing looks original on this one.
Tail lights and the stubby, upright tail on the spoiler say no younger than 85. It is possible to fit the later 86-88 tail lights on an older model simply because 82-88 are all the same in terms of the basic cabin and rear fenders. The doors also seem to be fitted with the oval bodied mirrors as opposed to the more angular or "rocket" shaped ones like what came with my own 85. Possible this is an LS in a party dress??
Bear in mind that 87 was the last official year that the rear wheel drive Monte was offered by the factory and that anything described as an 88 is a leftover that was depicted by the dealers as an 88 based on the actual year, not that it was new production for that year. Agree thoroughly that the VIN would settle the matter conclusively but it does not seem like the owner is going to be forthcoming with it.
As has already been pointed out, you can readily mix and match parts from various years within a specific footprint and get a complete car that is not a numbers matching ride but that does eminently end itself towards "Hot Rodding".
I say it's a 85-86 and half early run, 86 and a half later run and luxury sport had the rounded tail skin and lights and euro/triangle side mirrors and the dash insert and radio bezel are not the updated style
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