The skirt that should
- Oct 28, 2025
- 2 min read
Updated: Nov 3, 2025

Once upon a time, I was gifted a beautiful skirt. And, even though I didn’t wear skirts, I was excited about this one. When I took it into my hands, I imagined myself looking unassumingly beautiful. I got specific. In my mind’s eye, I had perfectly matched the new gift with a white top and leather sandals. I wore my hair up in a quick bun with wispy strands across my face that I didn’t seem to notice. And, I was thinner than in real life…Wow! This skirt was going to be amazing!
I hung the skirt in my closet and carefully packed it up each time I moved. The skirt remained after several decluttering sessions. When I came across it, I would say to myself, “Oh, of course, the beautiful skirt!” and quickly add it to the “keep” pile. But, I didn’t wear it.
The truth was, each time I saw the skirt hanging in my closet, I was pleased by its beauty and then felt uneasy. It belonged to an imaginary version of myself. A person that I thought I could be with the right effort. I hoped that I would one day need that skirt and so I kept it. And, for twenty-five years, I never put it on.
I parted with it one sunny Saturday while using the KonMari Method. When I held the skirt and asked myself, “What feelings am I inviting into my space by keeping this?” I had to admit that the answer was “regret” and “longing”. I had to let it go. With a sigh and feelings of uncertainty, I thanked the skirt and I set it in the donate bag.
Months later, I realized that skirts, as a category of clothing, had not crossed my mind since I had parted with my forlorn one. That gorgeous piece of fabric had been whispering disapproval to me. Why had I put up with it? Why had I kept an item that represented who I thought I should be? Or, in the words of the ever-wise Carrie Bradshaw, Why was I “shoulding” all over myself?
I do not think that I held on to aspirational clutter because I enjoyed living with feelings of inadequacy. I think I kept it because (oh, boy) I hoped that it would make me different. I hoped that the skirt would act like a good luck charm, creating the right conditions for my conversion. But, it contained no magic. Instead, it got in the way of my ability to live joyously with my real preferences. In this way, letting go wasn’t just decluttering- it was chiseling down. By removing what didn’t serve me, I uncovered my core. And, it was beautiful, too.
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