Inspired by JewelryGirl (and bored on a day spent home sick), I've decided to comb through my overstuffed wardrobe one drawer at a time and really be ruthless about what I'm getting rid of.
Here are some items I'm on the fence about. I'd love your help deciding whether to keep them (or, in some cases, whether to alter them.) Please excuse the creases (drawer space is too tight) and in some cases, wearing seasonally and stylishly inappropriate tops with summer bottoms.

Cords:
I'm cringing a little as I write this, but I do own two pairs of cords (pre-YLF). I've already determined to get rid of this first pair from Gap, medium wale and about 6 years old; I like the gray color, but the rise is too low and I think the cut is dated and unflattering. I'd rather replace them with some gray jeans: http://karip.smugmug.com/photo.....FvVZ-O.jpg
The second pair (from Eddie Bauer, a couple years ago) is dark brown and a very fine wale. The rise is higher than the gray pair and they have plenty of room without being too big. I'm leaning towards keeping these.
http://karip.smugmug.com/photo.....vqFW-O.jpg
http://karip.smugmug.com/photo.....mRU-XL.jpg

Clam diggers:
I got these on clearance mid-summer at Ann Taylor last year. They actually have an adjustable band/belt at the back, so I get no gape-age when I sit. Yay! But I'm starting to think they are a little too long.
http://karip.smugmug.com/photo.....Z42-XL.jpg
(Please pretend I'm not wearing a sweater - I was trying on every pair of pants I own and didn't want to change tops too!)
Here I rolled them to a shorter length. Better?
http://karip.smugmug.com/photo.....PRq-XL.jpg

My other pair of clamdiggers, on clearance two summers ago from Ann Taylor Loft, I know are too long - especially when I'm at a lower weight and they slide farther down my hips. They have wide hems that have little ties up the back (which are kind of goofy) so I think I'd want to tailor them above the original hem. I don't think rolling solves the problem because the fabric bunches too much.
http://karip.smugmug.com/photo.....yLT-XL.jpg
Rolled to shorter length:
http://karip.smugmug.com/photo.....uKr-XL.jpg

I found that my bermudas from last year still work great. I have two slightly dressier pairs (a tan plaid and solid black) from Target that I like. Not planning to give either of these away, but wanted to post something that works:
http://karip.smugmug.com/photo.....ggK-XL.jpg
I also have a seersucker pinstriped pair from Ann Taylor Loft that is nice for casual days, but I want to sew the slash pockets closed:
http://karip.smugmug.com/photo.....vo2-XL.jpg

Miniskirt (in the pants drawer because they have shorts built in)
This isn't worth keeping at all, is it? It seems kind of dated and even though I'm in my mid-twenties, my legs aren't fabulous. It's on the giveaway pile.
http://karip.smugmug.com/photo.....Hc2-XL.jpg