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I pretty much just keep it real. If it's more than 3 months since I've worn something, I know I'm never wearing it. So I get rid of stufff. And once you do it, you'll feel so much better. Just make a rule and apply it to every piece of clothing.. you'll see your closet shrink like nobody's business.
I am this way too, working in fashion retail. I almost always want something the instant I get rid of it. And now where I live, the closets are tiny and minimal so I literally have totes and totes full that I rotate seasonally.
Go through your clothes and pull some “maybes.” Keep them in a box for a month. If you don’t miss them, you can let them go.
I love this method. I need to do this.
For every new item I buy (ex: jeans), then one similar item must be discarded/donated. Works well for me and keeps me from accumulating an embarrassing number of jeans, hoodies, tshirts, dress pants, etc.