This is Part II of How to Purge/Edit Your Closet. See Part I here and see the next post for Part III.
Take a week or three off before doing the second round (Part III).
In the meantime, keep wearing your clothes as regular, or even step up your outfits with some effort and inspiration. Wear as many things as possible/convenient. See if you reach for and wear anything in 'purgatory'. If you do just put it back in your closet for now.
When you wear your clothes, make an effort to notice what you are wearing, how you feel in it, how it fits, even what would make the outfit better or more 'you'. Write down the things you need to replace or items that would make your wardrobe more versatile, and be conscious about shopping for only those items if you must go shopping. Try to minimize shopping, as that can just compound the problem. I personally recommend a full out shopping hiatus and focusing your energy on dressing your best with what you have.
Another really good thing to do is take a look at the number of things you have (we counted them up in Part I) and THINK about them. For example, work-appropriate tops. If you have 60 of them, and wear them 5 days a week, that is 260 days. This works out to an average of 4 wears per top. Is this the usage you really want for your money and storage space? A huge selection of options may sound like a great thing, but in reality it's causing waste of space, money, and even time choosing. The added stress really isn't worth the trade off.
As you do this the hope is for you to pinpoint what is working for you and what is not, and why. This is how I have been developing a great, cohesive personal style for myself!
A last note on fear- these are just objects. Letting them go is not going to hurt you, and most likely will liberate you. Fear of regretting a decision you make is hard to get over, but the worst thing you can do is not make a decision! Hanging on to STUFF you don't use for years is not the solution- the money is gone, and beating yourself up over it does no-one any good. Move on and do better in the future!