My two cents as a guy who is into fashion, but on a very short shoestring, and who appreciate well-dressed men and woman. As mentioned earlier, my wife owns a consignment store and I spend most of my free time there. The idea that some classic items can last ten years, or even five, is mostly wrong. I see all kinds of brands from the cheapest to the most expensive, and in most cases it is very easy to spot something older than two years, which we rarely take. Even "timeless" and classic pieces such as suits, blouses, pants, dresses, from the best labels (Dior, Chanel, Prada, etc.) lose their appeal after a few seasons and clearly show their age. This is also true to a lesser extent for casual wear like jeans and footwear. In my experience, very few pieces I own can stand the test of time, usually casual footwear and wool sweaters, but rarely dress pieces, unless you have them altered by a professional tailor which will cost you more than a shopping spree at your local consignment shop. Older, high end items and accessories that fall in the "vintage" category are a different thing altogether and while they can be very fashionable, they are not for everyone.