I am in the process of literally throwing out/donating 97% of clothes I own and am starting over with 4 dresses (of neutral colors) for the entire fall/winter seasons. I don't intend on buying any more. It's an experiment in minimalist aesthetics, simplification of life in general, and freedom from engaging in the retail world in any capacity.
The 4-dress only thing doesn't include tights and leggings, socks, scarves, and what minimal number of accessories I own (like... three necklaces). My leggings/tights are wonderfully colorful and varied, and I think all of these items will help me not be bored to death. In terms of shoes, I've always been a wear-the-same-pair-all-season kinda gal, so during colder months, I usually rotate between a pair of booties and knee-length boots, which is what I'll do this winter, I imagine. I threw out all outerwear except a trench coat, a gray wool coat, and a puffy long coat for the truly cold winter days. I'm not in love with these items so I thought of buying new outerwear, but that kind of defeats the intention behind the experiment....
It's been an INSANELY revelatory process so far, getting rid of things. Why do I hold onto things? What is the extent of my emotional attachments, what are they motivated by, and are they valid? What are the stories I'm telling about what certain things mean to me, and do I still believe them at present time? What am I afraid of losing by letting certain things go? How do I make a commitment and then negotiate myself out of it?
Also -- what do I want to communicate with my clothes? Am I sure about that? What am I afraid to NOT communicate? What is the actual desire behind wanting new things? Can they be met elsehow? What do I stand for, as a human being, and what do I aspire towards? How are those ideas/qualities reflected in the way I interact with material things that go on my body?
This endeavor is part of a bigger, general life phase I'm going through right now of setting things up in my life to be more congruent with the kind of existence I want to have (serene, peaceful, simple, attuned to enjoying qualities and internal experiences rather than things), which involves shedding a lot of outdated patterns/things I'm still holding onto. Specifically, this clothes project started because I recently moved to a much smaller living space and was faced with the giant (typical New Yorker) conundrum of what the hell to do with all my shit, given that, after unpacking, I literally had no room for about 4 boxes full of clothes. I was going to put them in storage.
Then I thought about how I don't even really like any of the things in the boxes. Then I chuckled at the metaphorical irony of having no room because my space is filled to the brim with shit I don't even like and then HAVING TO PAY EXTRA TO HOLD ONTO... things I don't even like? because I'm afraid to let go? why? (hello, my love life.) Then I went on a trip and had some epiphanies that told me that, actually, it's time for things to change in a big way. Then I started fantasizing about the wild sense of freedom that I would enjoy from owning so few things, the spaciousness (literal and metaphorical), the money I'd save... and the giddiness of facing a new sartorial challenge. (How to look cute every single damn day rotating between 4 dresses!) That was the kick in my pants. Or dress.