I'm a bit of a neat freak, and actually love to clean out my closet, but I also know that it can be a bit overwhelming if you didn't do it in a while, so I wanted to share my closet cleansing philosophy:
I always start by taking everything (and that means everything) out, this way you can be sure that you won't overlook anything when it comes to deciding what to keep.
Many people like to use the "throw out what you didn't wear in a year" rule, but I don't like that approach at all. I have a ton of things that I did not wear in a year, but sometimes there's a good reason. Maybe it just wasn't cold enough to wear that lambskin jacket, or you simply didn't have an occasion to wear that beaded dress.
I also hate it when people say you should only keep items that bring you joy. I mean honestly, what does that even mean? A white tee isn't likely to bring you joy, but it would still be a good idea to have one…
So my approach to cleaning out my closet has always been a little simpler: Just get rid of everything you don't feel comfortable in. This means everything that doesn't fit (and can't be altered) or just isn't "you". Think of it like this, if someone else were to pack your bag for a surprise getaway you wouldn't want to be miserable just because they reached for that one pair of jeans that's way too tight, or that cat sweater that makes you feel like an overgrown toddler.
I'd be lying if I said that I've been good about following this rule in the past, but during my last "cleanse" I really went for it. There was, for example, a pair of moto jeans that I just needed to have when I saw them in a sale two years ago…even though they were a size too big. I kept them because I liked them, but not because I liked to wear them, so last week they found a new home on Ebay, and I might use the money to invest in a pair that actually fits me.
So whatever it is that is filling up your closet, make sure that your wardrobe doesn't turn a good surprise into a bad one.
Peace, Love, and Lobsters