Singer Janet Jackson is forever reinventing herself.  This is not uncommon for stars who have been in the business for so many years.  A new and exciting fresh look keeps the fans coming back for more.  Look at Madonna and Cher  - it has definitely worked for them over the years.

When it comes to Janet and her longtime boyfriend Jermaine Dupri, well…their style sometimes leaves a lot to be desired.  I have found photos of the two that date back as far as 2004, and it seems that they haven’t always had bad style.  From time to time we have all been fashion challenged.

Check out all of the photos below.

Photos:  WENN

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Filed under: Celebrities, Fashion, Fashion Trends, Janet Jackson