Boy, if I had a good pair of jeans..I wouldn't need much else!
I guess you have to try on a lot of different brands & styles to find the pair made for you! With a great turtleneck, a nice velvet jacket, a couple nice cami's, a decent pair of boots and a smashing pair of heels I could live forever out of a suitcase. Bikini and underwear optional.
You might just make it under $2,000 == but knowing you you probably know all the best places to shop. Second hand clothing store are starting to pop up -- a recent article showed some designer clothes with the original price tags still on -- selling at less than half price.