I guess I never have. I remember going with my mom to drop off and pick up the dry cleaning about once a month or so, but it was only for my dad's uniforms (police officer). But at some point they either stopped caring, made more durable uniforms, or had a better washing machine because after I was about 12 or so I don't remember them using a dry cleaner anymore.
I liked our local dry cleaner because kids got free lollipops!
As for my own clothes, I don't really own anything that fancy. I usually wear nice sweaters and some slacks to work, but they are all machine washable. There are a select few items that I used to hand wash, but it was too much work for items that I don't really care about replacing that much, so now I just throw everything in the washing machine and dryer. I own a couple of dresses that I've worn once, but they haven't needed washing yet.