It's a common theme in fantasy literature (especially vampire stuff) to have immortals struggle with the changes in the world around them. This is usually presented as an excuse to have vampires running around in anachronistic outfits, and of course, an opportunity for deathless superheroes to have angst.
More recently, I read Vernor Vinge's Rainbows End. The main protagonist is an old man who lucks out in the rejuvenation lottery - he happens to have gotten old and frail in ways that medical science in his time is able to correct. His Alzheimer's gets reversed, bone and muscle growth is restimulated, etc. A big part of the book is the difficulty of Robert and his peers in living in the world that grew up around them while they were busy with thier careers. They've come out the other end of retirement and need to go back into active life again, and most of their skills and habits are useless or maladaptive.
Non-fictionally, I see a lot of the older programmers at work who have gotten stuck in a rut. They haven't really done much with any technology newer than the 70s era system (COBOL on a simulated mainframe) that they've supported forever. They go on courses for Java and C and PERL, and never use any of it. When they old COBOL system gets retired, so, I suspect, will most of them.
What all this adds up to is the conflict of personal inertia with the inexorable forward march of social and technological change. As we get older, we get increasingly set in our ways, and the gap between us and the world around us grows. My grandmother refuses to touch a computer. My parents have a hard time figuring out thier cell phones, and my mom still can't program a VCR. Society follows technology; the habits and forms of culture slide and shift as the media they ride on changes. Thus, as people stay with their comfortable, familiar tech, they lose touch with the bulk of society. TV and newspaper people in a Google and Twitter world. Eventually, as we age our peers start to die off, and our world just gets smaller and smaller. It's been my observation that an active social life seems to be what keeps people (in absence of physical impairment) from going squirrely - I've known several senior citizens who seemed sharp and well-adjusted until a combination of deaths and personal injuries/illnesses left them trapped at home alone for long stretches.
The conclusion that I come to from all of this is that, if I want to be alive and in possession of my faculties for as long as possible, I need to find some way to resist neophobia. I need to not be the guy who looks at every new technology that comes out and says "Bah! $THING_I_KNOW is plenty good enough for me! This new crap will never catch on, mark my words!" I need to keep trying new things and learning about new gadgets and ideas. I have a half decent chance of living into my 80s if I'm careful, and I don't want to spend the last 15-20 years of that unable to interact with the world. There's also the vague possibility of something amazing happening medically between now and then - anti-aging treatments, the Singularity, etc.
I'm 32 right now. I fought against getting a cell phone at first, and then for a while I resisted getting a futurephone. I have personality traits tending towards frugality and conservatism that could trap me if I am not careful. I didn't get Twitter when it started hitting the big time. I still hate facebook. So it's going to take some conscious effort to future-proof myself.
I had a bit of an epiphany a couple weeks ago. What I realised is, essentially two things; the the 90s are over, and that I don't care what teenagers think of how I look anymore. To unpack that further; the 90s were the decade where my sense of style developed. It's the decade where I was a teenager, and started giving thought to the message my outfit conveyed. The fashion of the 90s was really a peak of anti-fashion; the general trends starting in the 60s of rebellion against the established order of suits and ties for men, and dresses and skirts for women. The 90s in North America were the decade of Grunge, the fetishization of cheap, comfortable tough clothes - flannel shirts, loose jeans, and the military surplus made plentiful by the collapse of the Iron Curtain. The Dot Com bubble created an image of skilled professionals in completely casual clothes, and the scorn for the necktie reached, I think, it's most widespread level. Oxford shirts, ties, dress trousers, etc. all became symbols of the greed-obsessed yuppie/preppy culture of 80s TV and movies.
For years I held onto that basic idea - that to be "cool" required a rejection of those elements of fashion. I've tried to compromise in my choice of business casual appropriate outfits for work to take it as unseriously as possible. To hold on to the 90s unfashion. I realised that the audience I was dressing for no longer exists; youth culture has gone through emo/preppy phases, and ties have made their route through teenaged fashion. Todays teens weren't alive in the 80s, and barely rememeber the 90s. My peers, who remember the 80s and 90s, have, by and large abandoned the fashion ideals of our youth and "grown up". So, who am I trying to impress? I've been paying a lot more attention to the fashion choices on the TV shows that I watch (especially Chuck and White Collar), and realised that, hey, now that the 80s are dead and gone, some times a tie looks damned good.
Now, I'm still me, so I have to do it *my* way. While I couldn't define it, I do have my own sense of style. But there is definitely room for nice, traditional-esque stuff in there. Plus it's an excuse to wear a hat.
The other half of it is realising that I'm 32, and I don't care what teeagers think about what I am wearing anymore. For a long time, I have been trying to dress for what one might call the "teenaged gaze"; that is, I imagined that there was someone looking at me and evaluating my outfit. I'd walk past groups of kids and wonder if they thought my outfit marked me as a sellout or not. Really, though, I'm twice the age of today's teens, and there's so much cultural difference there that I just don't care what they think about how I look. I'm more interested in the sartorial opinions of my own age group, and for the most part, the rest of my generation has moved on. Some of that is "growing up" (and, by implication, "selling out" - the concept of which could be its own post.) Some of it is just not caring enough to maintain a seperate work and play wardrobe (the roots of anti-fashion at play!).
The end result is that for the next while, I'm playing around with wearing ties, suit jackets, tie pins, hats, pocket watches, cuff links, etc. I bought a new pair of boots on the weekend to supplment the latest iteration of the combat boots I've been relying on since I started working regularly. It ties in well, of course, with the neo-Victorian/Steampunk stuff I've been doing lately - thanks to that, I know what the proper traditional forms are now, to observe or subvert as I will. I'm mixing in elements from the 1920s and 1930s, and from thier stylistic echoes in the 60s Rat Pack.
It's still mostly black, with accent colours, and it's still "me", but it's nice to feel just a little more like I can do what I want. One day a week, I'm doing a dress-up day, to experiment.
Going back to the elements of aging I started this post with (tl;dr!), I think this sort of thing is important in staying afloat in the sea of culture. I can't let myself calcify and become rigid in my thinking, about clothes, technology or anything else. Stasis is, in a real sense, death in the long term. And another thing that's becoming clear to me is that I want to be around, as active and connected and healthy as possible, for a good long time.