I dye my hair a lot, in the past year it's been light brown, dark brown, brown with highlights, caramel, blonde with higlights, bleach blonde, natural red, bright cherry red and my current color copper red.
While I love the red it's a pain to maintain, I can have it dyed one week and it will have faded the next and let me tell you faded red hair aint pretty.
I also find I clash with certain colors, baby pinks in particular which means my beloved YSL Lingerie Pink lipstick sits unused.
So I have an hair appointment tommorow to change my hair to a cool deep chocolate brown shade, it will be a nice change for the colder months and it won't fade all that much, best of all I can wear my pinks again.
I never thought about hair colour clashing with certain makeup, it must be good to have a colour change to be able to wear different shades. I did go through a stage of dying my hair in my younger days, I had it a very similar colour to your about me pic, I really loved it but it just didn't go with my skin tone which was rather annoying.
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