I think that fun games with good art direction will always hold up reasonable well. Even PSOne games which people always seem to be particularly hard on.
If you play them on an HD TV and plug in using composite video, it will look irredeemably bad of course. Don't do this.
The 5th gen Resident Evil games get a lot of flack for (among other things) how they look. If you play any of the 480p versions (such as the GameCube releases or the PC versions or an emulated version) they actually look quite nice. The character models look a little dated, but they're nice and clean. And the pre-rendered backgrounds show a level of care and attention to detail that you don't find in many modern, fully rendered environments.
You might say that playing uprezed versions makes them no longer "old games", but I just look at it like watching a blu ray of a 1990s movie instead of the VHS. The core experience is still the same.
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