I have trouble answering this question because what might hold up for me could very well not for others. As much as I try to separate the nostalgia I feel for certain games from my actual thoughts on their quality, it’s undeniable that the first experiences I had with them, closer to the context they were in around their initial release, still colours my impression of them to this day.
With that said, I still think Shadow of the Colossus largely holds up. The scale of the boss encounters might not impress as much today but I think the muted world design and ambiguous plot are still stand-outs, particularly among the rest of Sony’s first-party lineup. Though I have my criticisms of the remake that was put out this year, I think that also offers a good way for folks to experience the game in (most of) its former glory without having to opt for an older console.
I would also say that a lot of the indie games I’ve played over the years stand a far greater chance of holding up (both in terms of their presentation & game feel). The smaller emphasis on looking cutting edge in contrast to a lot of the AAA gaming space means they don’t go out of fashion whenever there’s new developments in the visual fidelity of games. Though they still face some challenges in terms of standing out amongst the crowd. I’m sure if I were to show someone an older pixel-art indie game now they might immediately feel a sense of been there, done that.