Just wanted to pop back in to let you know what my stylist had to say about grey hair and letting it go natural. I've had grey since I was 22 and coloured my hair for 23 years before making the decision to go natural.
My stylist said the key to it being a reasonably painless process to grow out is to cut it short to start with. The whole process of growing out all my colour took only three months with trims to my super short hair every 4 weeks. After that you don't need to keep it short at all but ensure you have a modern cut and style.
He also said it's key that your hair be at least 30% grey before letting it go - that way the choice looks deliberate rather than you just couldn't get to your hairdresser.
As well, it takes a while for your grey, once all haircolour has grown out, to become shiny. The grey has been dulled by the colouring process and takes time to "breathe". However there are some ladies who have the grey hair that stays more flat and doesn't become shiny at all - that IMO is less attractive.
I actually tried growing out my grey about 10 years ago and I didn't have enough grey yet and it looked horrible. So we coloured it again and waited. This time I had more grey, it went shiny silver pretty quick and I loved it.
My other comment is I did have to stop wearing a couple of colours of clothing next to my face because my complexion looked different with my salt-n-pepper hair. As well, I had to change my blush colour and lipstick colour.
BTW - thanks for the shouts out Amy and Angie