I need the collective help and wisdom of YLF to figure out a way to get rid of at least 50% of my wardrobe--FAST!

Mr. G and I have listed our house in preparation for a move to a small condo on Vancouver Island. Ideally, we'll be out there by the end of October. When we built our current house, I made sure we had plenty of storage and closet space, but that decision is coming back to haunt me as I'm now trying to empty them out. Somehow, I've managed to amass 70 pairs of boots and shoes (scattered throughout the house), at least 30 pieces of outerwear/gear (this is after I purged all my deep winter stuff!), and an insane number of sweaters, tops, and bottoms (BUT only 2 dresses and 4 skirts--hmm, can you tell the way my wardrobe skews?). There is no way that our new digs will hold anywhere near that number of wardrobe items. I'm figuring that 100 items (including shoes, outerwear, gear, etc.) is the maximum number.

Over the last year, I've purged everything that doesn't fit, isn't in good shape, and isn't my style so what I'm facing is a closet full of fairly high-end, nice pieces that fit, would work for a coastal climate, and that I really like to wear.

Has anyone else every had to face this kind of purge? How did you decide what to keep once the easy-to-get rid of stuff isn't in your closet anymore? Where did you start? How did you start? Or should I just close my eyes and start grabbing stuff to put into the purge box? I'd also appreciate any tips from the Northwest coast fabbers about what I'd need for a rainy, instead of snowy, winter. I do have a pair of Hunter boots, an umbrella, and a waterproof trench...

Oh, and probably don't need to add that I'm feeling hugely guilty about my buying habits right now--which isn't making it any easier to get rid of stuff.