Jessica Simpson – 38

Jessica Simpson is a blonde bombshell, right? Yes, she is known for parading with cascading blonde mane and it can be easy to mistake her for a natural blonde. Indeed, Simpson is actually born a brunette! This picture on the left sure does give us a fright though! Perhaps it was fashionable when the picture was taken, but to us, it seemed Simpson was in dire need of a touch up to her roots with all that hair regrowth showing. And did she intend on having the striped look to her highlights? Yes, Simpson is far better off sticking to her current ‘do if you ask us!