I think trucks and cars stopped 'looking good' when they started to loose their appealing round female shapes and contours. Something very attractive that crawls under your skin got replaced with something that had more male and hard outlines which is arguably more impressive maybe.
Maybe the question should be: Which truck year(s) do you like and which do you like to actually drive daily.
I love the Art Deco and earlier Chevy trucks, but they are a bit too small for comfort as a daily driver. Nothing will hopefully ever seperate me from my 52.
After the 60s car and truck designs changed radically and had less recognizable character. Interesting how style and design of vehicles changed with the fast changing times.
Art and craftsmanship or the lack of it, seems always like a mirror or meter of society and the direction it is going.