{practicing.perfect}: Hairanoya

Sorry about the punny title; however, I need your advice. I'm taking a leap of faith with my hair.
I hate having my hair done. I know that seems weird but I honestly do.
I feel like I have been in the awkward growing out stage off and on since high school.

I've made several MAJOR hair mistakes during my lifetime, oddly enough these mistakes usually accompany major life changes.

In the 3rd grade I switched to a new school. To accompany this change I (my mom) decided I would look stunning with a bowl cut - think Thelma from Scooby Doo. To add insult to injury, I distributed my new school picture to ALL of my new friends. My best friend, whom I met that year, still has this picture and still taunts me with it today. There is no doubt in my mind that I will walk into an event in my honor one day & everyone will be wearing a t-shirt with that horrific picture printed on it.
In 5th grade, I begged my mom to get my hair permed. OH MY! My hair immediately turn into a dry, frizzy, triangular shape.
After high school graduation, my hair just barely recovered from the previously mentioned "perm incident," and just days away from heading off to Virginia Tech I cut my very long hair. No big deal, EXCEPT, I cut off nearly 12 inches of hair. My new hairstyle just barely reached below my chin & I was now off to meet all new friends.
After spending four collegiate years growing out the horrendous hair cut that followed high school, I knew better then to make the same mistake after graduating from Tech. But I needed a new 'do, so naturally I colored my naturally blonde hair....BLACK. Well not really, the plan was a dark auburn which depending on the angle looked black, or purple.
After very mixed reactions to the new hair color, including my mother telling me I didn't look like her daughter (which is ironic because my mom has auburn hair), I cut off all my long hair again. The new short haircut was actually very cut - but this leads me to the point where I am today. I have been awkwardly growing out this very haircut for 6 YEARS.

So now that you know my hair history - here is my dilemma.
I saw my stylist this past weekend for my standard trim, she was COMPLETELY appalled by my roots.
She asked if I wanted to update my highlights to which I swiftly responded no. I'm trying to go natural again.
When I was younger, my grandmother used to brush my hair and tell me how beautiful my natural blonde highlights were. She even went as far once to tell me, NEVER color your hair - people pay good money to have hair like this. Well of course I didn't listen - throughout high school & college, the blonder the better. I added bleach blonde highlights to my naturally ash blonde hair that then had to be maintained month after month.

I've done some research and it appears the growing out your roots is the new "in" style, it's called Ombre.
Here are just a few celebrities with the grown out roots.