I gained weight during our move and endless renovation. I put the smaller clothes in a holding zone. Hubby then made a deal with me that if they don't fit by this November (two year anniversary of our move), I have to part with them.
Well, once we had a working kitchen (this past January), I did lose weight! Though not quite back down to my previous "ideal" weight. So I got out all the clothes and many fit again, and made it back into my closet. Of the items that didn't fit, I was able to easily declutter about 90%. I held on to just a few cherished items that were still in good condition, and if for no other reason than to be able to test my weight loss progress.
Everything in my holding zone, which is dramatically reduced in size, is now one size smaller (probably would require a 7-10 lb weight loss). I highly doubt I'm ever going to see that size ever again, and I'm okay with that. And if I did see that size again, you can bet I would indulge in a complete wardrobe overhaul and buy all new stuff to reward myself...
But I digress. Back to the items that made it back into my closet:
Thing is, after a few months I realized I wasn't wearing ANY of the items that made it back into my closet!! The reality is that I will nearly always default to something newer, if I have a newer alternative. I just like new things, I guess. And also, my tastes / tolerances and lifestyle have changed. I want comfortable, forgiving and breathable fabrics. And shoes I can walk in. My lifestyle is veering more casual these days too. My color preferences are also changing, as I gravitate more and more to neutrals and subtle/murky colors rather than attention-grabbing ones.
So I put a bag in my closet and for past few months every few days I would put an item or bunch of items in the bag, whenever the fancy hit, and not just while dressing. In the middle of a conference call it would come bubbling up into my mind, "you know you are never ever going to wear that sweater again, the one that's itchy and the color was never quite right?" and once the call was over I'd go grab the offending sweater and toss it in the bag.
I wound up filling three very large bags. Pretty much ALL of the items that had come back out of the holding zone! It was quite the eye opener. And this included a ton of shoes that fit once again, I just don't like them!! I am preparing myself mentally to next massively cull down my handbag collection. In the back of my mind I've been mulling over which ones it's time to part with.
After I got rid of these three donation bags I then sat down and did a version of the Project 333 challenge. I divided my closet into "spring/summer" and "fall winter" and allotted myself only so many hangers for each (more than 33 -- but what would comfortably fit in a section). I organized my clothes within each section according to color as well. This method can help you decide what to cull and what to keep. This allowed me to see "gaps" and gave me some permission to do a little more shopping to fill them in, while also restraining me from adding yet another blue top.
I love everything in my closet at the moment, and it's all getting worn (weather depending -- it hasn't been cold enough for sweaters yet).