I got my first pair of glasses when I was seventeen, and wore them for a couple of years; when I lost them, I didn't replace them. They were very cute, sort of a Harry Potter look, but I really only needed them to watch TV or movies, my vision was OK to about twelve feet and there wasn't much to see beyond that.
When I started back to college in my later-mid 20s, I started having headaches and eye strain in class, so I got another pair of glasses. My near-sightedness had progressed so I was only good to about ten feet. Oddly, I think wearing glasses helped me stop drinking... I used to always take them off when I was drinking because it was too shocking to see the people I was with clearly.
I tried out contacts first when I was thirty and started worrying about looking old. But I didn't really like them, they made my eyes look bleary and the circles under my eyes more pronounced... the glasses cover the circles so well. And all the hoopla about cleaning fluid and cases and whatnot was boring. Sticking my finger in my eye was a lot easier than I had thought, though... after the first few goes, I got used to it.
And so my eyes have deteriorated just a little every couple of years... presbyopia, they call it. Now I can't see more than four feet clearly without my glasses. And this last year I started rocking the bifocals, with my corrective lenses I can't see anything within two feet of my face. When I wear contacts (which is mostly only when I'm wearing eye makeup, or am in costume), I have to have reading glasses. But I solved the ick of that by getting a lorgnette, which is the coolest ever way of looking at something.
My contacts, by the way, are incredibly comfortable one-use disposables...so comfortable I often fall asleep with them in and they still work fine the next day. The technology has progressed a lot, just since my first contacts, so those who tried them a few years ago and didn't like them might benefit from giving them another chance.