I've mostly had short hair my whole life. In college, I did let it grow long--to the point that it would hang past my nose if I didn't do something with it. Unfortunately, when it gets long, it becomes curly and wavy and does its own thing, regardless of how much product I put into it. It's easier to keep it short. Now, as I find myself with a growing tonsure, keeping it short is the better look. No combovers for me!
I also experimented with color when in college, too. I had highlights, dyed it deep purple and also burgundy. Because my hair is so dark, the colors only were noticeable in direct light. The time I had it dyed burgundy, they had to strip all the color out, then dye it--it was fine at first, but going to college in a southern California city on the ocean doesn't do well. The sun started to bleach it out and it turned this strange rusty color, so I had to have it re-dyed jet black to cover it. I cut it short at that point so it wasn't so noticeable!