Closet Ultimatum Update

You may have noticed that I am totally slacking on my Closet Ultimatum Challenge.  I think the items that I still haven't worn are stuck hanging in the closet for a reason - like I shouldn't be keeping them!  I've also been distracted by all the new things I got in Iowa at the beginning of August. So, here's my list of items and the current status:

1. Gap Pale Yellow Tank top - I'm keeping this, but it's getting demoted to a cami for wearing under other tops.  
2. H&M Floral tank top - going to Goodwill.  
3. LOFT blue sleeveless blouse - still on the fence.  I like it, but I hate to iron it. 
4. Ann Taylor knit top - another tough decision.  I got several positive comments about it, but I just don't think I will wear it very much, and I think it would sell nicely.  
5. Ann Taylor Coral Sweater - keeping it. 
6. Limited Pink and Brown top - selling it.
7. H&M Red T-shirt -keeping it.  I had forgotten that I actually wore this a few times recently (here and here). 
8. Gap Plum sweater - keeping it
9.  DKNY Navy top - selling it
10.  Target Tiger tee - I will keep it for now, and see if I wear it at all.  
11.  Gap dyed tee - I can't sell it, so I'll hold onto it.  I should probably make a rule that if I haven't worn it again in the next few months, I have to give it to Goodwill.  
12. Gap black skirt - selling it
13. Gap black linen skirt (worn here) - selling it
14. BR White skirt  - keeping it for now. 
15. Old Navy white skirt - the zipper is messed up, but still works.  I don't think I can sell it, so it is either Goodwill or keep.  I'm thinking about dying it, but I can't decide what color.  I think a cobalt blue or kelly green would be cool, I'm just not sure I can get the results I want.  
16. Loft graphic skirt  - keeping
17. Gap Purple skirt - keeping, but probably will only wear it with tights
18. Tommy Hilfiger green mini skirt - keeping it, but letting the hem out a bit. 
19. Ann Taylor floral mini - worn here and here.  I'm keeping it, but only to wear with tights. 
20. Loft geometric mini - worn here and here.   I'm keeping it, but only to wear with tights. 

I'm noticing a trend with my skirts being too short.  This is tricky when you are tall, so I probably just need to pay better attention when I am shopping.  Some of these skirts are probably at risk of being taken to the consignment shop just depending on what I decide the day I go.

Overall, I think this was a pretty good little Closet Clean-out challenge.  I'm getting rid of a few things that I have held onto for too long, and I was reminded about some items that have been forgotten in the back of the closet.

I need to finish sorting the rest of my closet - dresses, shoes, long sleeves, pants... the list goes on.  I might do another similar challenge once it gets colder.

How often do you clean out your closet?  Any tips?