I've been slowly paring down my non-business wardrobe, not sure if I can fit under $5000 but it's fun to take an inventory sometime - been organizing like this. I have more crap, but this is the "essentials" for me:
Seasonal outerwear - 2 pieces per season
Winter: Junya Watanabe/Duvetica down jacket, heavy wool coat (still looking!)
Fall: Margiela 5-zip leather, Lad Musician MA-1
Spring: Miharayasuhiro floral M-65, Paul Harnden long jacket
Summer: CdG linen blazer, Robert...