A reader came to us with what we imagine to be a fairly common dilemma: She wants to invest in a quality designer handbag, but also wants to make sure she picks one that is worth the exorbitant price tag. We think handbags are a little more important than other “investment pieces” (like shoes) and thus require even more careful consideration.

Unless you can afford to buy a new it bag every season, you want one that will withstand the passing of trends and continue to look amazing for years to come. We also think it’s important that you really, really love it and aren’t just buying it for status or–not that we think we have that much influence–because it’s on this list.

Also, remember that just because it’s marked down doesn’t necessarily mean it’s the bag for you. Lauren advises, “Don’t buy a bag that’s on sale unless it’s the one you really want. If you’re going to spend a lot of money regardless, pay full price for something you’ll love for a long time. I know from experience.” Here are five very expensive but, in our opinion, very worth it, handbags.