But you put that E39 M5 or '67 Mustang next to a modern car and it is still a damn good looking car.
For me, dated styling on a car is styling that I wouldn't buy if it is was a new car. Basically if Ford made an exact look like of a '67 Mustang new I'd love to buy it but if Ferrari made an exact replica of the 308 I wouldn't. It is kind of hard to explain what I mean. I mean the 308 is a good looking car but it definitely looks like it is from the late '70s and I don't mean that in a good way. The '67 Mustang is a good looking car that looks like it is from the late '60s but that isn't a bad thing in it's case.
Nah, see, you're still caught up in dated being a bad thing. It just isn't. Just because they look better than modern cars (which are by and large ugly) doesn't mean they don't look dated.