It's Time For A Change

So, the last time I was at the hair stylist's, we were talking about maybe coloring my hair. I tried dying it a little darker this summer, but what ended up happening was, it changed my undertones, to a more reddish brown than my normal color. Now, my winter roots are growing out more visible than they normally have, and I don't like it. So, we were talking about coloring the hair darker, and maybe leaving the bottom or some pieces the color I have now, a la the pictures I have above of Alexa Chung and Mila Kunis. I just feel like my hair has been virtually the same for so long, and I need a change. Recently, I've been styling it messier than I normally do, and I love it! What do you guys think? 

Kisses, Helena.