The Trials and Tribulations of Spring Cleaning: Clothes

I'm in need of clothes I like, and instead I have drawers and a closet full of stuff I either don't wear anymore, or that needs to be thrown out since it looks like it's been worn by someone weekly, since 1974.

Because I don't have a clear sense on what I really have, and before I blow a bunch of money on new stuff that suits me, it has become increasingly clear that I'm better off starting by getting rid of the useless stuff.  While it will feel like I have "less" it will just be easier to find my go-to favorites, and I'll have less trouble closing the overflowing drawer of tank tops I have.

So I think I would end up with 3 piles that I'd need to figure out what to do with:

Trash:

• I love this, I wore it to death, and now it wouldn't even suffice as a layering piece it's so worn out. 
• This is misshapen/stained/ripped/I inadvertently shrunk it in the dryer and even a 4 year old couldn't fit into it now.

Donate:

• This doesn't fit me anymore/I don't like it anymore and it's in good shape, someone might be okay with buying it for cheap.
• This is a quality item but I have no use for it, someone might buy it for a bit more at a nice thrift shop.

Not sure what to do:

• This has sentimental value and I'm not sure I can part with it, but I'm never going to put it on, or wear it outside of my apartment such as endless amount of promotional t-shirts...the most comfortable and/or funny ones I do wear when I run (my Miller "I tapped that glass" t-shirt is always a crowd pleaser).
• I like this but haven't had the opportunity to wear it in a while, an I can't anticipate when I will wear it, did I mention I think I like it?
• This USED to fit me, and I really like it.  It is now too small, and I hope I'll be thin enough one day to wear it again.
• This USED to fit me.  It is now too big, and I hope I never fit into it again...but if I do, I'd rather be miserable due to my weight, versus miserable to have to go out and buy new "bigger" things.

The not sure what to do pile is where I get stumped, not as clear cut as trash/donate.

Do you have recommendations of good organizations that take clothing donations that are a fundamentally good company/charity/etc?

Should I just donate everything versus worrying about a couple higher end things for a thrifty/nicer second hand store?

Do you have recommendations on how to decide to purge/keep those hard to part with items?

Feedback is much appreciated!   Thanks y'all...

Until next time,
E