I would dress basically the same too... (My patented $400 winter outfit)
well...
I would have more extravagant jewelry
My watch, bracelet, and necklace will cost more than some people's yearly salary
-EDIT-
What I wear now:
Silver Necklace + charm ($200)
Silver Wacth and Bracelet ($200)
My Kobe's (shoes) ($130)
Nice pair of pants ($100)
Nice Shirt ($30) or Jersy ($50)
Boxers ($5

)
Jordan Jacket ($200)
*counts money*
god dayam... that's a little more than $400...