Love these posts!
I think the key phrase here is 'sunk costs' because that money is spent as soon as you purchase the item. This helps me to let go more easily.
Selling the more expensive pieces can ease any feelings of guilt too!

I have slowly gotten over sunk costs after wasting so much time with consignment appointments and Resale Rejection. That is especially if it doesn't fit/ isn't flattering.
I have a harder time with things I have too many of but they all fit and go with outfits but I'm not wearing them all. I am so finicky about proportions that I like gray top A with these pants and gray top B with those pants , or this jacket length not that one, and so on, or neutral pieces, maybe " Essentials" that still fit great. So it's really hard for me give those up even though I have tried, pick the top 8 of 10 or whatever. I have to really hammer myself to do one in/ out or replace one item with another.
I tried to do my " if in doubt, edit it out" but I'm not good; I DO ascribe to, if in doubt, wear it out ( out of the house) as that sometimes really clarifies a flaw in fit or feel.

The reason I want to see the items is so that I can convince you of why they need to be passed on, and to who.

I am an okay closet editor, I do two big ones a year and occasional other ones as the mood takes me.

I like to think of others using my clothes who will enjoy and appreciate them. So I either donate or sell early on if they are clearly a mistake OR keep and wear until they are basically no good to hand on. Occasionally I may hand on if I am tired of an item after a couple of years but I feel if I am over a fashion trend, others likely are as well.

It is also okay to keep some pieces that you are unsure about if you have the mental and physical space to do so.

Sterling, your solution of consignment and the women's shelter sounds like a winner! I usually take my nicer pieces to consignment too.

I operate similarly to texstyle: If I have something that is decent quality and fits well but I'm just not loving it, I store it for a year or two (I live in a four-season climate). I have surprised myself at what I have gone back to as my style shifts. I have also pulled pieces out of storage because they go well with a new item that lacks a lot of companion pieces. If after a couple of years the item is still not making me happy, off to consignment it goes.

If items are rejected for consignment or if they don't sell, I may keep them around if I think they might come in handy for a costume party. I attend a few of these a year, and sometimes it's nice to have a stash of old clothes to start the costume creation process. I do try to get money for them first, though.

One thing I should mention: Every time I give away stuff during a closet edit, I remind myself that I'm doing the best I can and that it might indeed happen that I have regrets about giving away a certain piece later on. But I remind myself that I can't know the future, so it's OK if I mess up and give away something that I wish I hadn't given away. Giving myself permission to make a mistake helps me move ahead with getting rid of items.

Angie => This Coach briefcase was the item that was foremost on my mind when I originally drafted this post.

I bought this in ~2000. I think I bought into Brand Marketing because I was convinced I had to have it. It is heavy leather. I use it about once a year (to justify keeping it). It is not designed for laptops and multiple reports. Oh, and the weight is then doubled. The whole thing is just poorly, poorly designed.

As I mentioned above, I had to have this bag. It marked a major career transition for me (Smittie's reference to emotional past). Those emotions are one reason I can't just donate it. I have to somehow know it is landing in a good home.

Another item is this necklace. I loved it in my 20's, but at some point, I lost interest in this style of jewelry. The picture does not do it justice. It really is a gorgeous piece of jewelry. People comment on it whenever I wear it, I just find I prefer pearls or no necklace at all. At least, the necklace does not take up much room.

Your thoughts are welcome, Angie. I especially would like to know who would best benefit.

Smittie -- You are right. Despite my earlier denial, I realize this morning that ALL of the items I am struggling have immense emotional ties. I think a lot of them were purchased at around the time of some major life change or transition. They marked a major goal or achievement.

WOW. This puts everything into a whole new light.

I might be able to remove them from my wardrobe, but keep them in a keepsake box.

Sterling those items are beautiful and hold wonderful memories for you. I have some jewellery that I never wear that I bought when I accomplished something (got into graduate school, graduated from graduate school, etc.) I keep them in a special place.

I think I am going to put together a keepsake box.

I know that Coach bag. As a matter of fact, I wore one to interview for my first job out of graduate school in 1999. It was borrowed from my office mate, she told me everyone will be impressed by my briefcase.

The necklace is a no brainier. I would keep it. Find a way to get rid of the briefcase, you will never use it again. Too impractical.

Thanks for the pics. I get your dilemma.

My dear, Sterling. Just keep these items as sentimental pieces. We ALL need them to complete our style stories.

I have always struggled with editing my closet and the more I try to edit at one time, the more I dig my heels in and simply can't let go. I do think it's ok to hold onto a handful of pieces for sentimental reasons, or when it's pricey, was a workhorse in the past, but for whatever reason is taking a season "off." Of course, there is a fine line here, hold on to too many things and you end up with a closet of nothing to wear for "right now."