If I had the time and space, I would amass my entire wardrobe into one giant heap. That heap would be divided into a "yes" pile and a "no" pile.
The "no" pile would be a sad goodbye to miniskirts and size eights. I can't turn back the clock and by the time I lose 20 pounds my "skinny clothes" will be out of date, so I should let someone else enjoy them. The "no" pile would also include anything I forgot I owned or hadn't worn in the past year. And I would definitely include anything worn out or stitched up so many times it should have bolts coming out of its neck.
The worn out stuff could be used for rags. The tiny clothes and the I-had-to-buy-this-even-though-I knew-I-would-never-have-a-place-to where-it clothes could be donated to Goodwill or the Salvation Army or given to friends or sold at a yard sale or in a consignment shop.
The "yes" pile could be divided into possible outfits. This way, I would know what my wardrobe lacks and maybe think of a few items that would bring it up to date. I would make a short list of versatile, stylish pieces to buy.
This plan isn't feasible for most of us. But you can start by dividing your winter clothes before they go into storage. Keep the classic and flattering items. Discard what didn't fit, what you never wore or what's out of style. You will free some space and give yourself the opportunity to fill in the gaps in your wardrobe next fall with a few well-placed must-haves.
Of course there must be leeway for nostalgia. I would hang onto a Hot Topic shirt that got whistles way back when. I would keep a couple of things that I could associate with specific memories. I would also keep a few of those irresistible, no-occasion pieces, but I would make it a point to wear them in the near future.
Take a tip from the bad economy: downsize your wardrobe then plan a cautious upgrade. Gain hope from the "yes" pile, and let that big pile of "no" remind you that this is not a time of excess. It's time to appreciate what we have now, and spend carefully in the future.