Reese Witherspoon
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Reese has been slowly getting away from her ultra-golden blonde to that of darker tones.  With several different shades ranging from a medium blonde to light brown, Reese has quite an interesting menagerie of colors.

This could be a slow transition to introduce a brunette shade.  At least the stage has been set.   Light shades of chocolate would look great on Reese as her tones can handle quite a spectrum of them.