Closet Clean-out

My closet is getting jam packed. I figured there is a ton in there that I don't like. I decided to go through it a little.
I barely went through any. I tried on everything before it goes to the Goowill pile.  My problem is I liked a lot more than I remembered liking.

Another problem was a lot of the clothes that used to be too big now fit or are too tight. Lots of clothes that did fit (that I do not want to get rid of) are too tight now.  I need to organize/categorize or something so I don't get confused what fits now.

Above is a collage of most of what I tried on.

What is your process for going through your closet? Do you do it all at once or go through parts at a time?

I have made posts before about trying on old clothes, but they weren't this extensive. In September 2010, I said that I hoped I'd get through 2 feet of closet on the one side. I did not even make it through that 2 feet today.

1. I also have a pink shirt like this. I haven't worn it in a few years (Possibly April 2007). Should I get rid of it? 
2. Pants are slightly tight. They used to be too big. In December when I went to the Steeler game, I wore pants under these for multiple layers. 
3. I haven't worn this sweater in years. I always think it'd be too small. I don't know why because 2 years ago when I went through my closet I realized I liked it. I think I got this in high school. I wore it in early college.  I definitely haven't worn it in the past 6 years (since the calendar site has been around.)
4. Gray skirt - was too big a year ago to a year and a half ago. Fit great 2 years ago. Fits great again now. Will make it back into the rotation. Purchased in 2009 from Kohl's (size 4)
5. casual long sleeve black shirt. fits great. comfy. not sure why I didn't wear it for lounging all winter. (NY&Co)
6. Black Pants that I bought in 2005 when I interned. They got huge or were huge. I didn't like how they looked like they were falling off of me so I put them in the other closet. Well they seem to fit a lot better now. They are comfortable. They will go into my rotation. They are long so I have to wear heels with them. I think for a period of time I was only wearing flats so that is another reason they haven't been worn in years. Spring 2007 or earlier was the last time I wore these.
7. Purple shirt. It is too tight and too short. It has been for years. I haven't worn it since 2003 maybe. Getting rid of it. It is from Wet Seal. It used to have silver sparkles on it but I wore it too much and they wore off.
8. Black skirt - was too big a year ago. Fit great 2 years ago. Fits great again now. Will make it back into the rotation (Purchased 2009 from Sears)
9. Shirt that looked like 2. I loved this shirt in college. It is too casual for work so then I stopped wearing it or remembering it to even wear on the weekends.  It is now too tight and a little short and since even when it fit, I stopped wearing it, it went to the Goodwill pile.  It is a nice shirt though.
10. Gray Pants. 6L from Old Navy back in high school.  These got huge for awhile or didn't fit right or I didn't like how wide leg they were. But now I like the fit. Except 2 years ago I went through my clothes and made the same realization but never wore them. Perhaps documenting everything this time will help me remember. 
11. White Pants. I wore these for the first time slightly before knee surgery in 2009. I have a matching blazer. They make me feel so dressy that I avoid wearing them. Or if it is rainy I avoid them since I often have to walk between buildings. Now they are slightly tight but just ever so slightly. Like if I go back to the weight I was just 2 weeks ago, they'd be more comfortable while sitting. I kept these. I am noting the fit. We'll see how long until I wear them. 
12. Brown Tee- purchased in 2003 or earlier. I haven't worn it in years... like 7 or so. But I like how comfy it was and how casual so I'm keeping it. But I think I said the same thing 2 years ago and didn't wear it.  So if I don't wear this in the next month, I'll give it to goodwill. 
13. Express Jeans. Size 29. Stretchy. Got way too big.  Not big now that is for sure. Perhaps after wearing them 1 hour I would say something different though. They sure make my butt look big or my butt makes my butt look big and the jeans don't hide it.  I took these jeans out of the spare bedroom closet and put them in my own. At least I don't have to struggle to button these like my other jeans.
14. Red Express long sleeve T. Haven't worn this in awhile. Not sure why. I will add it to my rotation around Christmas and layer it under cardigans when it is cold. Just so many options for it. So I'm keeping it.
15. Sweater/dress shirt combination. I thought this was too loose around the waist. I didn' try it and just assumed it was boxy. For some reason I thought it was. Now I'm disappointed I didn't wear it all winter. I can't even find me wearing it on my calendar site later than 2008. I wonder if I did.
16. Another brown tee. Purchased in 2003 or earlier. Keeping it like the other one but if I don't wear it in a month, it is gone.
17. VS Jeans.  These were pants I ordered in my first VS order when I didn't know what size I wore. They were a little big. Then they got really big last spring. Now they fit good, but they are too low rise. If I bend, I swear I'll moon someone.  I kept them though. Perhaps with a belt they will be better. Also I'll wear a really long shirt. At least these jeans don't require me to suck and and tug really hard to get the button to button instead of sitting 4 inches apart like it wants to.
18. Black shirt. I like it in theory but it has these markings where your chest should be but my boob is set lower or bigger than the marking is so it is stupid. I hate it. I don't know why I kept it. I have worn this shirt maybe twice in 4 years.
19. Light pink Express Shirt. I wore it a lot in college but since it is kind of see through, I didn't wear it once I got older. I often thought that I could wear a cool pattern underneath but never did. I usually went with a pink, nude, or white cami underneath.
20. Pink Tee. Going to keep this for working in the yard or working out when I do not want a tank top. It isn't as nice as the long tees that are around now but it isn't that short. I have it bunched up/tucked in so that the buckle on the skirt is seen.
21. Purple button down shirt. I got this in 2006. I always hated it. It isn't form fitting enough. My mom even altered it so the hips don't have wings but it needs darting around the waist or something and I'm not going to fuss with it.
22. Pinstripe pants. Purple stripes. I have a blazer to match. The pants fit but are too short. I am keeping them. If my butt and gut get smaller then they will sit lower and not be too short. Since they match a blazer, I will keep them.  I probably haven't worn them in years. 

Did I decide to keep too much?