I came across an interesting article which has been around for a while discussing "Pizza Flyers: The Height of Good Graphic Design?". It’s well worth a read and also the comments. I’m not sure I agree with everything in it but it is certainly an interesting thought exercise.
I work on developing financial software for traders and there is a “battle” between developing a user interface that is clean, usable and presents data efficiently and “just make it look like Bloomberg or Excel”. A lot of users likes to go with what they know whereas the developers often try to “bring it up to date”.
So, even if the user interface looks like it was written in the 80’s if it means the trader can do their job efficiently is it good or bad design?