Contemplate the tag.
Perhaps you haven’t gotten around to wearing the item. That is fine, but give a good, hard think about why you haven’t worn it. You’ll probably need to understand your shopping habits. I have a few names for these shopping syndromes, like Label Dickmitization (you bought it for the label despite its shortcomings) and Price Wasn’t That Bad Brain (the price wasn’t that bad despite the piece’s shortcomings). The list goes on. Perhaps you are one of these people and need to dig into your true feelings before you swipe your credit card.
Think about why you’re tied to certain items.
There is most likely a lot of emotion here. Sometimes, there is a guilt complex. Did your mom give you an ugly blouse, but you can’t bear to say goodbye? Was it a gift? I’ve coined syndromes for these conditions, too! Mommy Issues Hoarding Syndrome (MIHS) and Gift Guilt Syndrome (GGS). Attempt to separate yourself from the object. If the going gets tough, some Enya, a beta blocker, and a walk around the block may be in order. Remember: If the item is taking up unwanted space, it is taking up unwanted spiritual real estate, too.
Deploy the expiration pile tactic.
With a last resort pile, and you must adhere to a few rules. First, put all the items you are unsure about in a heap (or neatly on a rack or in a drawer), then wear the piece and test it out. Write down or take a mental note of how you feel in the piece. If you like how you feel, keep it. If you don’t like it, say goodbye! Don’t abuse the pile! Be discerning.
Think about things that aren’t fitting quite right.
This rule does not apply to items that don’t fit due to major size fluctuations, but rather items that have never really fit quite right to begin with. We all have them: The blazer that you bought at a sample sale with a friend who convinced you the bloated shoulder pads made you appear “confident” in a Michael-Douglas-Wall Street way, but actually left you looking like an out-of-work David Byrne impersonator. In an ill-fitting item, discomfort radiates from your very essence.. How can you be 100% present if you’re tugging at a shirt or thinking about a button popping out?
Take it to a tailor.
If items aren’t fitting exactly how you want, but you still see some hope in them, bring them to a tailor. Just don’t let those pieces accumulate. My editor has a pile of things by her front door that need a tailor’s attention; I tell her that’s not a solution, that’s just another problem!
Start small.
Every item that goes is a step towards a cleansed closet is a step towards a cleansed you. For the closet-cleaning curious, I suggest implementing the time rule: Give yourself 60 seconds once a day to find one item to part with. By the end of the week, you’ll have seven things to sell, donate, or throw away.

