Questions to ask when evaluating a particular item:
• Have I (or anyone else in my home) used this item in the last year?
• Is it broken, and if so, is it worth fixing? And will I actually do so?
• Do I have a particular use for this in the near future?
• Would it be difficult or expensive to get another one, or would I sincerely regret parting with it?
• Do I love it? (Or does someone else in the family love it? We don't want to start any family feuds here, much as you may wish to rid yourself of a leg lamp or, in my mom's case, my dad's taxidermy pieces, which she calls "D & Ds" (Dead and Dusties).)
• Does it make my life easier?
• Do I need it (either for function or, with paperwork, for legal purposes)?
• Would I rather have this item or the space that it occupies in my home?
• Would I keep this if I were to move? In other words, would it be worth packing up, carrying around, and unpacking in a new space?
• Would someone else I know enjoy it more than I do?
• How many other items do I have that serve the same purpose?
• Is it my style now, or is it just something that I liked at a previous point in my life?
• Does it fit (your body, your space, your style, your needs)?
A "yes" to any of these questions might constitute a reason to keep the item in question, while a "no" might be a good reason to toss it, but remember that it's ultimately up to you to decide if the item should stay or go. There are no hard-and-fast rules here. If you're still undecided, why not err on the side of putting it in the box for now, just to see if your emotional attachment to it fades over the next few weeks. There will be a time that you can rescue it if you change your mind.
As you evaluate, try not to think about how much an item cost. Just because it was expensive does not mean that it's useful or relevant to your life now. Also, when you go through items that are particularly tough to part with, I suggest not holding them for lengthy amounts of time. Set them on a counter and look at them, or leave them where they are. Holding items can temporarily heighten your emotional attachment to them. It's part of the (very clever) reason that salespeople try to get you to try things on or to test them out.
As a parting tip, if you are really having a hard time paring down your possessions, you might want to set aside a block of time and invite a close friend over for tea or cocktails and a de-cluttering party. Your friend won't share the same emotional attachments to items and might be able to give you some unbiased perspective on their use or beauty.
(Image: Craig's Tiki Hut House Tour)