The very fact that so many people find it dated is what makes it dated. "Dated" is nothing more than an opinion.
No. You're proposing a radically relativistic stance toward design aesthetics, and that's just not how it works. If
@BillJ looks at the SR-71 Blackbird and thinks it looks "dated" to the 1980s, when it's actually from 20 years earlier, he's wrong. (Nothing personal, Bill!) If I show someone a Pierre table by George Sowden and that person says it looks "modern," that person is wrong — and I could counter with a Noguchi table, which actually is from the modern period. If I show someone a Proust chair by Allesandro Mendini and that person says it looks "dated" to the 1700s because of its Rococo form factor, again, that's wrong, by about 200 years.
It is, technically, accurate, to say that the TOS
Enterprise dates to the 1960s, simply because that's when it was designed. I'm not disputing it; that would be silly. But, so what? To say it
looks dated requires doing what
@Groppler Zorn has been attempting and showing how it looks similar to other identifiable designs from the period — which it doesn't. it's not a purely subjective matter. Context is critical.
(There are aspects of the design that I think Jefferies borrowed from postwar futurism, the same movement that gave us, e.g., the architecture of LAX and the Space Needle. He used those aspects in new and different ways, however. And it's silly and pointless to say that those designs couldn't or wouldn't be revisited in 300 years and therefore don't still look "futuristic." Just as it's silly to say starship designs from any other show (or movie, or game) look
more futuristic. It's the future. It's all imaginary until we get there.)