I'm sure we've all owned a pair of Converse in our time, but that doesn't take away from a potentially intimate, unique relationship that each owner can have with the shoe-in-question. I, for one, have an amazing -- and have had amazing -- experiences with all of my hi-tops and lo-tops over the years. Here's why.
I think I can speak for everyone (yell if I'm only speaking for myself) when I say that we feel a certain safety and heritage when we participate in the using of a classic item. Not a blasé, fad-laden item, but an item that has been around for years passed and years to come. I always liked the thought that Beaver Cleaver and his buds were playing baseball in these in the 50s, or the fact that these shoes managed to suffice as suitable basketball shoes for the professionals for a relatively long time post-Cleaver era. They're simply something that will always feel right and are deeply engrained in personal and external history alike. I say stick with classic colors like off-white, black, and red.
2. They Look Good.
Bottom line, they look good. The way the lip of the shoe can be substantial or fall behind the laces can completely change the shape of the shoe and the mood of an outfit. They are perfectly robust, narrow, rounded, straight. Also, they look good with anything, really. They can pair down a lace dress or compliment a pair of denim cutoffs also indigenous to the same season.
They can make an outfit pseudo-unique not because of their invariable ability to appear on nearly every "soft grunge" or bona-fide hipster Tumblr, but because they grow (well, not literally) and age with the individual over the course of their wearable existence, contouring to their foot. That, but also they have surely been there in light of many Firsts in a person's life.
4. They're Relatively Comfortable.
Compare them to, say, a pair of heels, these shoes are relatively comfortable. That being said, they are quite thin and have very little support, but the canvas gives the false impression of ankle support. And that placebo is enough for me.