I'll be honest... I care about looks. It's not my #1 determining factor, but I'll admit they matter somewhat to me. I always loved the look of the WJs, so I built one. I always thought my '11 Silverado 2500HD would look better with a solid axle and 37"s, so I'm doing that too. Of course, both of those choices had many other factors that went in before looks. I could write a book on why I chose the WJ, but the short-ish version is great size (much smaller than modern SUVs, or even 4-door JK/JLs), linked coil-sprung solid axles front/rear, V8, nice interior with "luxury" features... and looks cool. As for the solid axle swap, well obviously it's going to articulate much better than the stock IFS, allows moving the axle center line forward to fit the larger 37"s without actually lifting the truck much more at all, gives me an option for a selectable front locker, allows for a front free-spin (so I can run "2wd Low")... and it looks cool.
Anyway, I guess I'm saying that looks matter, and anybody who says they don't is just lying to you or themselves. But, function should come first, second, third, fourth...
So, when it comes to the '85 vs. '99 let's talk function first. Of course, there's the elephant in the room too: budget. For 99.99% of us, budget actually comes before everything else. IMHO the question becomes, which will function better for you within your budget. Obviously the '85 looks cooler, but it also might be more functional if you're into trails that require more articulation. In just about every other way, the '99 will be functionally better. Of course, if budget isn't an issue, the '85 could be made just as nice to drive, just as reliable, just as fuel efficient, etc. or the '99 could be solid axle swapped. :p
There's also the question of how handy you are with a wrench, and do you have to deal with smog. I'm in CA, and the '85 would be a nightmare here unless I kept it bone-stock as far as engine... in which case it'd be a super-slow turd with terrible MPG. That alone would move me towards the '99.
-TJ