RE: work clothes -
I do a pretty good job of setting a strike-price / fill-order when it comes to work clothes. I've been able to keep a good stock of work-approved slacks/khakis/button-downs simply by buying them whenever they are below a certain price-point..generally that's $9.99 for khakis, $19.99 for slacks, and $5.99-14.99 for shirts...usually from BananaRepublic, Gap, Macys, or Nordstrom's Rack. Same holds true for shoes. And I scored a $350 blazer for $29.99 at Macys earlier in the year. It helps that I'm an odd size (tall/skinny w/ big feet), but I think the deals are there for others. Just set a standard such as "I'll only buy X item if it's below Y price (or Z % off)" and then fill the closet as appropriate. And try to stick to Jacob's color-matching consciousness..