I think you should want people to see you in pieces you've already worn because others will be able identify your soul as these pieces define you. I'm not saying you should wear the same shirt everyday but don't keep a record of who's seen you in what. If you feel like a bombshell today, then wear the Christian Louboutin heels that have been collecting dust in your closet.
Never purchase a piece for art unless you plan to frame it on your wall. Fashion can be beautiful and when it comes to style, it's all about wearing what you purchase (unless you are decorating your apartment). We think we purchase art to wear but then we consider how much care goes into wearing the piece because we'd be so upset if someone were to spill something on our $3,000 Oscar de la Renta dress.
But how stupid must we feel after investing in a piece that we save for a "special occasion" and then find another reason NOT to wear it. Yes, you should be careful about where you wear your pieces but if it results in you never wearing the item then maybe we are investing in an item that is way beyond our budget. The point of an investment is having something that will last because you know you're going to wear it often or you'll wear it infrequently so you know you will almost never have to purchase it again.
Some of us shop based on trends and not style. So we're always shopping to get the latest thing because we never want to be "out of style." It's fine if this is the kind of person you are but I think once you are able to understand the true importance of style and learn how to shop for yourself, you'll realize how ridiculous shopping the latest trends sounds. If a trend fits you, I say go for it but don't try to fit in with the rest of the world by purchasing what's hot and then leaving it in your closet because no one is wearing it anymore. No one person is the same mentally or physically with another so we shouldn't wear the same things.
I think it's smarter to invest in pieces that define who you are and are within your shopping budget. I may not be able to afford to spend $80 on these Steve Madden lawful sandals but I have that amount in my shopping budget and they reflect my edgy side so I've invested in the shoes. I know I can get two summers out of them if I wear them just about everyday instead of spending $100 on 3 pairs that I'll have to replace before the summer's over.
Spend the most that you can afford on the pieces that you love and that reflect you to build a great wardrobe. It's time to shop for replacements when you evolve as a woman and re-define your style or when the pieces eventually fall a part. There will be times when you truly have nothing to wear for what you want to accomplish and when you need cheap items but I think most of the time this is the best way to shop.