Not all at once but season by season? My plan is to drop my extra weight then buy either the bulk of a new wardrobe or several new items to complement what I already have. I love getting good deals so I won't be hitting up Saks or Bergdorf's and the like (except for perhaps a pair of shoes I saw in a catalogue). But I've never stepped foot in places that 'upscale' before but may this one time. My style is classic and semi-corporate. These clothes would be for work. I make good scratch but value money so won't go crazy but I am looking to update my wardrobe! How much would you justify spending over the course of the year? $500/$1,000/$2,000 a season? I'm talking about the whole kit and kaboodle (from new undies on out).