I think Angie gives really good advice about this when she talks about buying for your real life.
The connection might not be obvious at first, but here's how I see it.
If aiming to "invest," the way to go is with iconic fashion items -- but only if these icons make sense within your real life.
Examples: If you are working in a law office and need to wear a well-tailored suit several days a week, you probably have a good grasp on what is current and good quality in tailored suiting. And if you don't, you need to look around, talk to people and figure it out. Once you find "your" high quality suit, you will wear the heck out of it for at least three years, maybe even a bit longer. And that is a lot of wears; it will earn its cost. Especially if you love it. If it lasts longer, wonderful!
Meanwhile, if you are a stay at home parent, you probably wear jeans a lot. So forget the cheap jeans. Or at least supplement them with a pair or two of premium jeans. Buy the best fitting, happiest pair you can afford in a current cut. And wear the heck out of them! Three or five years is a pretty long cycle for a pair of jeans. If you are really lucky, they will last longer.
Other potentially iconic purchases:
- The trench coat (Burberry?)
- The navy blazer
- The leather moto
Etc. But this is climate and lifestyle dependant. No point in buying that trench if you live in the arctic or the desert. You don't need the cashmere scarf if you live in Hawaii. That's why those "10 items every woman needs" lists are ridiculous. We all have different needs. Sometimes people pay a lot for an item they rarely wear -- and guilt ensues. If you wear something a great deal, there's no need to feel badly if you need to "retire" it after three years or five years.
I also think it is worthy paying more for any item that looks unbelievably great on you and makes you feel magically like "yourself."
You know. The kind of thing you try on and don't even have a moment's hesitation about. You want to wear it NOW. The tags are off!
Even if the cut isn't the most current a year or two from now, you will probably be able to bring it up to date with the way you style it, and you will still look fantastic.
For some, this will be related to figure flattery. For others, it will be more dependent on how well the item expresses a certain style persona.
There are also wild card items -- arty or avant gard or vintage pieces that have so much character they will stand the test of time and mix into a wardrobe of modern classics (if that is your core style). If the fit and quality is high on those pieces, they might live in your wardrobe for decades.