Gosh wouldn't it be lovely to spend money on clothes and know that they are going to increase in value over time! LOL
I used the term investment dressing as it is used in the fashion press to refer to buying the best quality items you can afford for your own personal pleasure as alaskagirl said, rather than as a way of showing off or trying to climb the social ladder.
The theory does sound appealing to me but you wise ladies have mentioned some of the downsides to this approach, Jenn mentioned fluctuating sizes, Dee suggests possible mishaps, would you almost be too scared to wear them as they represent such a big investment? Also lack of variety was pointed out by Cheryle and Kerry, another thought from Aliona was how long things will remain in style.
Deborah, CocoC, E, Style Fan and Gryffin all have encouraging thoughts on the topic, Gryffin you had me on the Helmut Lang Smoking Tux!