Lessons Learned From My Old Clothes

It was a warm afternoon in July when I came to a very important decision.

Relative to other choices people face in their lives (whether to take job, move somewhere new or end a toxic relationship) it wasn’t wasn’t that serious. It still was impactful. For me, this decision was months in the making. It started as a cloudy concept and slowly snowballed into an urgent necessity. 

I decided to donate a lot of my clothes to Goodwill. No big deal right? People did this all the time. For me, this wasn’t an easy choice. After taking a serious look at my wardrobe I instantly grew attached to nearly everything I owned. Each article of clothing wasn’t just something I wore, they were a part of my history and story. The clothing I had been clinging to and preparing to wear into oblivion carried a piece of me like DNA. They had an origin and memories were attached to them. They were worn during many phases and experiences in my life. 

Why now? Well, for one thing, life was entering a new chapter and I didn’t feel like the same person anymore. Times were different and I wanted to embrace the change by letting go and shedding a layer of skin (and clothes). It also just seemed like an opportune moment to replace these clothes with new ones, or perhaps other used ones from the same Goodwill store that I was about to visit. 

As I scrubbed through my closet and dresser the unwanted clothes began to pile up. Before bagging them up and giving them away, I stopped and gave them a long look. In a gesture of not forgetting and honoring them, a blog post felt like the right thing to do before parting ways.

Besides a link to my spending history, they also taught me a lesson and gave me a mini slice of wisdom that I didn’t want to lose. 

So, if you don’t mind me going on a small tangent about things I used to wear, here are some stories and lessons I learned from my old clothes: 

I bought these pants at a Zara in Murcia, Spain in 2015 with the intention of finding something of high quality, stylish, and inexpensive. They looked cool and were affordable, but they were impossible to iron and faded after a few washes. I ended up buying a different pair of pants after a few months. Lesson: Sometimes it’s best to spend a little extra on quality one time than to spend a little less on multiple low quality items. 

This shirt was my “one day” dress shirt. I purchased it thinking that one day I would like it and eventually wear it. That one day never came so it was time to let it go. Lesson: Don’t hold onto things that don’t bring you happiness in the present.

This sweater was a random discovery when I was living in Spain. I stumbled upon a thrift store while getting lost between alleyways. I was teaching English at the time and I thought the look would make me appear more “teacheresque.” I looked more like a poorman’s version of Mr. Rogers who was hopped-up on caffeine but it did make me feel more professional. In the end I felt the quality of my work improved. Lesson: Dress like you ARE the person you want to be, even if you don’t always feel like you are.

I bought this tank-top in the Spring of 2016 at a Pac Sun a few days before going to Coachella with friends. I didn’t think I would wear it after the festival weekend, but somehow it stayed with me for over five years. It brought some wonderful memories but I didn’t identify with the item anymore. It felt like it was time for another 20 something year-old to sport it.

Lesson (1): Listen to your intuition and heart. Lesson (2): Pac Sun is an underrated brand. 

This had been one of my favorite shirts since buying it at Proof Lab in Mill Valley sometime in 2016 or 2017. For years this would be a go-to t-shirt. It never shrunk nor had it developed any funky aromas. Overall it was a wonderful shirt. The only reason why I gave it away was that I felt satisfied with the experiences we’d shared and it was time to spread its positive energy with someone else. I packed it away with love, feeling like my new go-to shirt was out there waiting for me (maybe at Proof Lab).

Lesson: When we are generous, we receive generosity. 

I bought this shirt with stimulus money. I was unemployed and being supported by the federal government at the beginning of the pandemic. It was an uncertain time but this shirt gave me a feeling of hope and optimism. I felt good wearing this shirt because it fit me really well. Now that I had gone back to work I felt like a new chapter in life had started so I want to donate this shirt to the fashion gods. I hoped it would connect with someone in need of some luck. Heck, the brand was Lucky so that must be a positive sign.

Lesson (1): Be thankful for what we have and don’t ignore the simple pleasures in life.  Lesson (2): You don’t have to play baseball to wear baseball shirts. 

Some other items included a pair of black sweats that were so worn-out that the pockets were missing. They were good for comfort but bad for going to the grocery store or library. A couple shirts which were gifts from friends were included and the only reason why I gave them away was because they had shrunk and therefore I felt they were now meant to make an 8th grader really happy. 

Clothes, if you one day learn to read, I just want to express my deepest gratitude for keeping me warm and for being with me over the years. We’ve been through the best and worst of times together. Through the joy and loneliness you stuck with me. You didn’t let the rain or other unexpected foul weather get you wrinkled (except the pants, you never got unwrinkled). You’ve seen me in my highs and lows in life. There were times when I wasn’t my best self and you didn’t judge me. You just gave me a hug and that was more helpful than I could have imagined. As I write this segment I’m becoming aware of another lesson you’ve taught me: Actions speak louder than words. You’ve never spoken to me, but based on all you have done for me, I feel blessed.

Please be well, stay clean, and I hope someone else appreciates you as much I do. 

The bag with my clothes and memories was now closed and I’d just parked the car. It was time to let go and drive away from the Goodwill parking lot. 

I was excited for my clothes and for myself to start a fresh chapter that perhaps would smell like lavender detergent.

Minutes later I returned home. To my dismay, I realized I had just given away everything in my closet.  

Final lesson: Remember to own at least two shirts, maybe three.

The End 


Thanks for reading my blog! I appreciate you. Do you have an article of clothing that brings you back to a special moment in life? 

Have a great day and take care.


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