I don't think of my stuff as investments, per se. I sometimes rationalize my purchases by thinking about the cost over a year, as in if I buy something that costs $365, then it only costs me $1/day (which is less than most people spend on coffee or other little things).
Certain things I think of as more like disposable because I know they're not going to last as long (like the cheapie tops I used to buy at the mall to wear to bars/clubs back in college). And if something is less expensive, I tend not to get upset if it breaks or doesn't last (my $20 Old Navy scarf is fraying, and the only reason I care is I love the color, but I never expected it to last past this winter since their stuff is not high quality).
All that said, I never buy something with the intent of reselling it. If I buy shoes, jeans, or purses, I plan to use them without any specific expiration date in mind. Once I decide that I don't want an item any more, whether it's because I wore a hole in it from overuse or because I'm just tired of it, then I either give it away or throw it away. I've considered selling a few things on ebay but ended up just giving them to people.
To be fair, I don't have any Hermes or high end bags, so I might feel differently if I had a closet of Birkins.
But even with high price items like a car, I don't expect it to sell for the same price after I've used/driven it for a few years. Hee, that's partly because when I love something, I use it a lot!
My main thought on something holding its value is price as it relates to quality. If I buy an expensive item and it falls apart after a month, then I'll be annoyed. To me, that's something not holding its value.
As charleston-mom mentioned, sentimental value is also a factor. If I love something, no matter how cheap or expensive it was, I want it to last forever and I'll baby it in the hopes of extending its life. I have a cute $20 leather purse I bought in Berkeley almost ten years ago and I still love it. The strap broke recently so I had to have it repaired, but it was worth it because the thought of not having this purse anymore is terrible!
I just read
this interview with Karl Lagerfeld and although this quote is in response to fur, it can apply to a lot things:
If you cannot afford it, just forget about it. Don’t use it as an investment piece to show people how rich you are. Use it like a cheap knitted thing. It’s like a big stone. Lucky you that you can have a big stone, but if it troubles you financially to have the stone, don’t have the stone.
If you can afford it, OK. But if you think it’s an investment, then forget about it.
Keep in mind that Karl says a lot of crazy things and take it with a grain of salt!
