How to let go of loved garments when clearing out?

[EveSix]

I'm supposed to be clearing out my clothes.
I have too many.
They need to go.
I love them!
How do you get rid of items you really love? I keep thinking of reasons not to cull: it is so comfortable, it is such an unusual garment, I wore it for a special occasion, someday soon I'll be required to wear a jacket just like it, it's a collectors item, my dad bought it for me, and so on.

Any ideas for how to override this irritating tendency and let loved garments go?

Surely that can't really be true of the majority of things though?

I do think for me it is just about being brutal, all those things can be true to varying degrees and it still not actually be something you genuinely need in your life. If i've not worn it and it isn't genuinely practical I do get rid of it and have come to really enjoy clearing out. I used to hoard clothes terribly and much prefer less clutter now it's gone and it's nice to have so much space at home.

If it's sentimental to the degree its being kept forever I would take it out of my wardrobe and store it elsewhere but for me it would really need to be special, not just something I wore that I attribute a good memory to.

Examples of things I kept last time that I am not currently actually using are things like an expensive weatherproof waterproof coat (expensive to replace, always will be useful at some stage), a black dress suitable for a funeral that I've worn to one a number of times. Everything else goes if I don't need it, don't reach for it or don't actively know of what i would wear it to.

Things that I don't wear out but are comfortable I choose a few and 'downgrade' them to my loungewear drawer to wear around the house until they wear out.

If i have items that are similar I whittle it down to which of those I like best (black jumpers. white shirts etc) and just keep one or two.

Any shoes that remotely rub or I can't walk a decent distance in also go.

Marie Kondo's method helped me to recently get rid of clothes I'd been hanging onto for 15 years +. (Recommend her book, The Joy of Tidying). Turns out thanking my possessions for the joy they had brought me in the past was literally all I needed to do. It's a few months on and I don't miss them or regret donating them all to charity- I wouldn't have worn them again but now they have a chance to bring someone else joy. She talks about how clinging onto clothes but not ever wearing them is doing them a disservice... Weird but true!

I am fairly brutal getting rid of things. But I also enjoy passing things on to someone who will enjoy it. I recently passed on some old goth clothes and shoes I wore when I was younger to a girl I work with. She is headed to uni in a couple of months. I like to think she will be wearing them and they will be living again.

If it's linked to something particularly special or poignant you can have it made into a teddy bear!

Thank you for the suggestions, I appreciate it.
In every other area of my life I tend to be practical and pragmatic, so this is an annoying anomaly.
The fact that oldest DD is now the right size for some of my clothes, and really loves to mess around with different looks makes it sting to get rid of stuff.
I actually think I've got some kind of doomsday thing going on as well; "Stuff like this isn't going to be made / easy to come by / affordable in the dystopian future coming over the hill." Must work on that.

For things with memories attached, could you take photos of them, to keep that connection, before letting them go?