(Sorry, not that kind of out.)
There is no good reason to have as many clothes as I own. Later this year I will be living out of a backpack while I travel for a month and I'm hoping to repeat the backpack era again at the beginning of next year, so the seasonal wardrobe change is a good time to give my closet a thorough cleaning and asset reduction. Let me plan what I will be travelling with and see how I go over the summer on a significantly reduced wardrobe.
I've realised out two problems I have when cleaning out my closet: guilt and love. The solution to these problems is multiple sorting in two phases.
Round One, Five Piles
There are pieces of my wardrobe that I love. They fit well, they serve multiple purposes, they have memories attached. In one way or another, they make me feel good about myself and about owning them. That is not a problem. But what is a problem is letting go of them when they are well and truly worn out. So when I clean my closet I have a pile for "Things I Love" and everything I really love and feel I need to keep goes into that pile.
There is a second pile for "Basics I Think I Need." These are things that I wear frequently. Black leggings. Tank tops. Various foundation pieces. Socks.
And there are clothes in my closet that I'm not in love with at all or don't wear much any more but don't want to part with. It would make me feel guilty to get rid of them. They were expensive or gifts or I thought I'd love them but didn't or they don't fit unless I am at my very thinnest (but then they look terrific). They go into the "You Are Hurting My Feelings" pile.
There are always a few items that I know I need to give away to a better home. Those go into their own pile to be packed into a box or bag for donation. This is the "Give Away" pile.
Off to the side is "Trash Bag". This is for any clothes that have obviously outlived their time and would not be welcome at a clothes swap or donation box, like odd socks, ratty pajamas, and items with damage. It stays pretty empty in the first round.
Round Two, Consolidation
Now the Things I Love and the Basics I Think I Need piles get another look. I start by making some outfits. It feels a bit like a fashion edit, 5 Pieces = 25 Outfits! Can this item I love be coordinated in multiple ways? Yes? Put it away in the closet. No? It's Give Away for you my friend. And then a final check - are all my coordinating clothes in good condition? I tend to wear things out, so if something's shabby can I (and more importantly will I) repair or refresh the item? If the answer is no, then it goes from the closet to the Trash Bag. Bye bye!
And then the You Are Hurting My Feelings pile gets sorted. If I am feeling strong and ruthless, I use two existing piles - Give Away and Trash Bag. If I am feeling weak, I make a third pile, Maybe Another Day, for things that are going back into the closet for another try.
At this point the trash bag is getting full, the closet is restocked and it is time to attack the coats, shoes and accessories.