Going Darker

I typically have always been blonde (except one time when I decided to dye my hair dark dark brown and it was the biggest mistake of my life.. OK not that big, but still).

I normally only get my hair highlighted about twice a year and cut about 4 times a year. I'm weird, I know. My hair just doesn't need it as much because typically the sun will lighten it and I don't really struggle with damaged hair. 

Anyways, that's all to say that I need to go get my hair highlighted and I was thinking of adding more of my natural color in. (I have a light brown natural color, I describe it as squirrel colored). Nothing too stark, just a gradual darkish color. (No, not ombre)

Of course the first place I look for inspiration is Pinterest which really tempts me to want a change for fall!

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What do you think? Should I go darker?