I always have to have both my toenails and fingernails painted. I don't ever match them, however, but I HAVE to have them painted year round. Even when I don't wear sandals. It's just something I've always done. In fact, when I see women with longer unpainted/natural nails, it grosses me out. I don't know, I'm just really weird that way, but if you're going to grow your nails out to be a lot longer than normal, then paint them! They look gross unpainted and long.
In fact, my dad raised me to believe that chipped fingernail polish is cheap and tacky. And he's right! I was painting my nails every 2 days because they always chipped and it bugged me. Now I just started getting them dipped and I love it! They last forever and always look fantastic.