The fact that The Matrix is 11 years old, and the N64 14, have similar effects.
I wonder if part of it has to do with that the older you get, the more of your life you remember. When I was 5 (which I don't remember), I probably couldn't remember what it was like to be younger than 4 - in other words, I could only remember 20% of my life. When I was 10, I could probably remember about half my life. Now that I'm 23, my earliest memories are around age 7: I remember more than two thirds of my life. But I think that, while growing up, I sort of got used to most of my life being unremembered - so when I'm faced with how much of it I now remember, I somehow feel uncomfortably far from my memory horizon. Thinking about the fact that I've lived more than half my life since the release of the N64, which I remember reasonably well, is disorienting.
Now I wonder whether that always works, or whether there's something special about the last twenty years that makes 1990 seem surprisingly recent. To me it seems that culturally not much has changed since the 1990s; the fifties, sixties, seventies and eighties all have distinct cultural vibes, whereas the 1990s, the 200xs and now our new decade have all sort of blurred together. You wouldn't look _that_ silly today wearing clothes that were fashionable in 1990, and as for 1999... well actually some of my clothes are from 1999.
I think we can blame the internet for that. Before, time created a huge gulf between each stylistic period as they receded into the past. It was very difficult for someone in the 70's to experience much at all of 50's culture except through the nostalgic ramblings of old folks (which idealized these times heavily).
Now the net has created for us a "long now" where cultural elements are basically assimilated and never forgotten (to emerge later as idealized nostalgia). I think its the fist little nibble of the singularity at our heels.
Perhaps, or perhaps it's just a return to a more normal pace of cultural evolution after the rather unusual 1940-1990 period where an awful lot of stuff changed rapidly.
After all, I can't see much difference between the fashion and culture of 1910 and 1890, though perhaps they'd seem larger to someone living through them.
I think it's just a question of perspective. I think an awful lot of stuff has changed the past 20 years. Think of the effect of Internet. Hell, right now I'm sitting in a Starbucks (also unexistent in 1990) in London, UK and sharing my thoughts real time with people all around the globe! How awesome is that! There are a lot more examples.
In terms of popular culture, musical genres such as boy bands of the 90's, drum and bass, goa, nu-metal have came and gone; some truly remarkable movies have been made, think of Forrest Gump, The Matrix, Amelie or Trainspotting.
More specifically my home country (where I don't live anymore unfortunately) has seen the end of communism and people had to grow used to a capitalist environment which affected every aspect of their lives.
And yes, believe me, you would look extremely silly if you've worn 90's style clothes so please don't.
To be honest I'm pretty sure the clothes office workers around here wore to the office in the 70's are about the same today too (although you'd probably see more ties and suits then than now).
I remember being surprised the first time I heard someone refer to Duke Nuke'm 3D as an old game (if I can remember getting it when it just came out it's surely a modern game!)
