How do you wear your Converse shoes? With pride, of course. Converse, in particular "Chuck's," are more than just a shoe--they're a way of life.
First, find a good pair of Converse shoes and most shoe stores carry Converse. Chuck Taylor's are still under $40, so pick your favorite color. I recommend getting shoes with ankle support.
Wear the shoes as often as possible. I had a friend that wore his Chuck's to a wedding. He said those shoes are part of his personality, why wouldn't he wear them? I also heard a story about a guy that wouldn't even take his Chuck's off to lose his virginity. Chuck's are against the grain and give off an air of anti-establishment. Converse are about youth, enjoyment and being yourself.
Enjoy your Converse. Of course, a pair of shoes does not define who you are, but when you decide to wear Converse you're sending a message. You're saying, "I don't need to succumb to trends. I'm going to stick to something tried and true."
Don't lose the attitude. As I've gotten older, I wear Chuck's less and less. I simply need something with a little more support. However, no matter how many pairs of New Balance I go through, there will always be a pair of Chuck's on my feet in spirit.