During the 1990s the preppy Tommy Hilfiger brand unexpectedly became the uniform for teens in what became known as the urban wear market. Attempting to capitalize on this new found appeal among the hip hop crowd, Hilfiger altered his styles and adapted his advertising and promotional strategy accordingly. However by 2000 slumping sales and Tommy hilfigers own desire to be regarded as a "true designer" prompted a return to the brands preppy routes. What challenges would you have expected the brand to face during the transition and why?