As far as deciding what to keep once you have established meaningful place to donate (and they won't judge or ask questions-- they'll be grateful) look up Marie Kondo and her process of letting go of clothes. I know you probably won't heap every single item onto your bed, but that helps take in exactly how much you have to deal with and how important it is to minimize. Let the clothes connect with you. If it doesn't, or you haven't worn it in a year then let it go with gratitude. It's a very cool and even spiritual process and you'll end up with items you cherish most or the ones that make you feel best. Good luck. You've got this.

Edit: typo