Toss it? Fix it? Keep it?

How do you know when to get rid of something? I mean sure, some things are easy... but others, not so much.
I can't seem to find the balance between simplifying and saving. I feel wasteful getting rid of things that just maybe needed a little love or things I never really used. At the same time, I feel cluttered keeping everything. I get angry with myself when I see something sitting unused taking up space, but I can't seem to bring myself to deal with stuff.

1. Clothing - When do you deem a piece of clothing 'used beyond repair'? I have some jeans with some holes, do I keep them as yard work clothes? Do I really need 4 pairs of work pants? Do I keep that jacket that I've been meaning to hem for the past 4 years? What about those pajama pants that have a hole in the crotch? What's being wasteful and what's being thirfty?

2. Technology - I feel bad getting rid of technology. I mean, it's expensive stuff! Well, it was expensive. Now it's worthless, yet I feel guilty getting rid of it. Most of it won't even be able to be used by someone less fortunate. Like my ZipDrive. That thing cost a fortune when it first came out! Now, the measly 100MB disks are a complete joke! You can't even store a photograph. Plus, with cloud storage, there is hardly any need for any external physical storage anymore... Also, do I really need two printers? Those were expensive too. Or what about a scanner from the early 2000s? The image quality is probably so bad that it's useless. Regardless of the fact that I haven't used it in five or so years...

3. Shoes - I have some shoes that I wear a lot. Like holes-in-the-toes-worn-down-ripped shoes. I feel like the second I get rid of those I'll need to wear them for something. But I can't be classy and look professional if my shoes are ripped. Then there are the other shoes. The shoes I bought because they were on sale. The shoes that were so cute for that one outfit that I never wore. I can't seem to part with those either. I see some people with tons and tons of shoes and I think, "Well, at least I don't have that many!" But then, I see people who have just a few pairs. Perfect, adorable, nice pairs. And I want to be like them. I want to be a simple-fun-cute shoe wearing girl.

4. Bathroom supplies - Lotions, shampoos, makeup, nail polish, cremes, washes... you name it, I probably have a sample of it. I've been doing better about getting ride of the old products, and using up the mostly empty products. Yet somehow my stash never looks smaller.

5. School supplies - I think I could open a small campus bookstore. I have so many books from classes that cost me a fortune to buy. I'm not done with school yet, so I am afraid to get rid of any of them. I've tried selling them back in the past, but they're not worth anything anymore. (Don't even get me into my rant about textbook companies!) And office supplies! How many pencils, pens, erasers, staplers, stickies, notecards, rulers does a person need? Apparently a gazillion... I can't seem to part with them because I know I'll need them eventually but really, my collection is getting quite ridiculous.