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!

Una, yes! I haven't put it in exactly those words, but I do choose my clothes for the experience of wearing them. For sure!

I have had a few splurges in the past few years and it turns out "investment dressing" (buying very expensive items with the expectation they will last for many years) is not for me. I have splurged on some fairly expensive things that I have worn and loved and I don't have any particular regrets, but it turns out I get bored with even my super faves. So I don't really want anything to last for 10 or 20 years. I want to be on to the next thing within a reasonable time.

Not really. I look for a reasonable quality in my clothes, but it wouldn't be feasible or affordable to spend a large amount on one item - I'd have nothing else to wear!

I think that you should buy and wear what you love-- if that means a pricey or designer piece that is of good quality that you can afford and you won't be skipping a bra or underwear refresh or be going without black pants to afford, buy it. I think the problem comes from the expectation that it will still be usable and loved by you in 10 years. Two or three-- sure? Five-- it is a good bet. Longer than that and so many things can change-- lifestyle, climate, weight, health, styles, etc.

To me, the only things worth investing (aka splurging) in are clothing or accessories that don't change much in style over the years - like bags or coats or Frye boots. But other clothing items seem to change style fairly frequently and I like to change my look more often than 1-2 pieces a season. Plus, I don't want to have "invested" in expensive clothing when that style will feel dated or tedious to me. I'm thinking of BF jeans and ballet flats which I'm tired of but which I didn't spent that much on.

The other problem with "investment" clothing is that nowadays, high prices don't always equal high quality