Okay, I'll go photo by photo:
1. Intentionally faded black jeans. These are okay. They fit you nicely, and I could see them going with a lot of things. How would you feel about replacing them with some dark black jeans instead? I've always found it difficult to match faded black jeans, but I think that's just me (you know me, I like really vibrant solids). If you feel like they are too big, pitch them, or maybe get the waistband taken in until you can find something to replace them with that you like better (I do this a lot with my wardrobe).
2. Tahari Jeans. These look like they fit you alright in the picture, but I'm not a fan of the wash. Plus, it sounds like you already don't like these that well and they stretch out. I vote toss.
3. Calvins. Nice, I like the wash on these a lot, and they are very "smart casual." They look like they fit you nicely too. Keep these.
4. Sevens. These a great! I think you should wear these as your "casual" jeans in place of your more faded pairs of jeans. These are very flattering, and could be worn dressed up a bit or more casually. Keep!
5. Newport News Denim Skinnies. Are these too big for you? They look like they are kind of bunching funny around the zipper area. If I remember correctly, the only way you wear these are tucked into boots with a longer tunic top, right? If so, then I don't think the bunching is really a big deal. If you have nothing else to wear with boots, then keep these. If you don't really like them, keep them until you can find something you like better.
6. ON Jeans. Not a fan of these. I think your Sevens are a million times better and more flattering. Toss 'em, or keep them for gardening or painting.
7. Brown Limited Cords. Yep, toss. Too big.
8. These. I have to admit that at first I didn't read all the way through your post, I just opened up the photos and started looking through. When I got to this photo, I though, "What the hell ARE these?" and then I scrolled down and saw you had posted, "Embarassed to own." LOL. You crack me up. Anyway, don't throw these away--burn them. I can't tell what they are made of, but I'd replace them with a lightweight pair of cotton-linen trousers for summer, or maybe a very lightweight cotton pair of bootcut chinos. J. Crew makes a good summer chino that comes in several colors.
9. ON Cargos. See #8.
10. Esprit Tan Cords. I actually like these a lot. How do you feel about them? Is it that you just can't figure out what to wear these with?
11. Newport News Cream Skinnies. I think I would like these worn with boots and a tunic top, but it sounds like you aren't getting much use out of them. Maybe you're finding that you just wear the blue NN skinnies more? If that's the case, I say pass them on. I wonder though--would you find you wear them more in the spring, when colors tend to lighten up a bit? I think they would look great with apple green, and that color is fabulous on you.
12. BR Black Denim Trouser: Are these a bit big for you? Maybe it's that it looks like they are hemmed for heels, and you're not wearing any heels in this photo so they kind of pool at your feet. If they fit okay up top, I vote keep. The color still looks nice and dark, and I'm thinking that shape would be very flattering on you with heels.
13. AT Black Slim Cords. I think these are okay. It's hard for me to see the pants because they are so dark on my monitor. If they fit up top, then keep them. Are these hemmed for heels as well? These are a bit on the casual side because of the pocket detail on the front pockets. I like that though. You are so lucky you can get away with that.
14. Grey wide legs. These look too big around the crotch area, and so they are bunching kind of funny. Do they fit you okay? It could be the way you are standing though, I'm not sure. I'm sort of torn, but I'm leaning towards getting rid of them, but only because I think you look so great in your jeans. I think you could find trousers that fit in a similar way. Maybe you can keep them until you can replace them with something else.
15. Softer grey. Are these like yoga pants? I think they look good for yoga and exercising and stuff. Lounging around the house. Taking your daughter to school.
16. AT Light Tan Full Pant. These look way too big on you. I vote toss.
17. Black Pencil Skirt. Great! Definitely keep. Nice to see you in a skirt again!
18. Kenneth Cole Dark Denim pencil skirt. Keep.
19. Black and Blue Large Print Knit. Keep.
20. Stitch Skirt. Keep.
21. Faded Denim. Hmm...I'm torn on this one. I much prefer your Kenneth Cole dark denim pencil skirt to this one. But that could just be personal taste. The skirt looks like it fits you alright. Maybe if you keep this one, it would be good for going to the park and running around with the kids, or beach vacations and stuff.
22. Esprit Wool Plaid. Nice, keep.
23. Plum Tweed Flare. Great! This is a wonderful shape for you, because it really balances out your top half. Definitely keep!
24. Target Cream Cord Skirt. It's so weird seeing a cord skirt with totally bare legs! I think if you always pair it with tights or something, it's nice. I love cream.
25. Unidentified Skirt. What is this made of? I prefer your other skirts to this one, so if you are going to get rid of any of them, I say it should be this one. The print just seems too tiny for you or something. I can't put my finger on it.
26. Tahari Cream and Pink pinstripe. I like this one. From the description of the color, I think it could be nice for Spring. Give it a shot and see if you wear it a lot this coming season. If not, then pass it along.
Whew, I made it! Hope that helps. I'm looking forward to your part two of closet cleanout.