How To Deal With Guilt During A Winter Closet Cleanout

why does a closet clean out bring up so many emotions?

we should take a break

Break ups are hard. Sometimes it’s the righteous sacrifice of, “I Will Always Love You,” ala Whitney Houston. Sometimes it’s getting away from an unhealthy situation like “Toxic” by Brittney Spears. Sometimes it’s bitterness from being left behind like Alanis Morrissette and “You Oughta Know.” And maybe the hardest of all is being left behind like Sinead O’Connor and “Nothing Compares to You.” And maybe I went through a lot of breakups in the 90s.

A closet purge can bring up surprising emotions as we let go. It’s like saying goodbye to dear friends (the worn out favorites), breaking up with toxic exes (they never fit right), and unburdening guilt (gifts and expensive shopping mistakes) all in one afternoon. And sometimes it’s a moment of acceptance of where and who we are now, as ugly or uplifting as it may be.

Letting go of a favorite item that is no longer fit to wear, that was gifted to us, that was a shopping mistake, or accepting that we aren’t that size or that person anymore is enough to make anyone avoid a closet purge. They can be emotional, stressful, and too much truth to handle.

the emotional side of a closet clean out

I’ve gone through all of the emotions attached to purging items. Those expensive items you feel guilty getting rid of? I’ve done it. The gifts you feel guilty purging? I’ve done that too. That expensive thing you splurged on and still has the tags attached? I have some. Acknowledging that I would have to take extreme measures to ever button those pants again? Been there. Recently. Cleaning these items out of your closet is not easy, but it is worth it.

I’ve done a few major closet purges in the last 3 years, and they were HARD. I did it in rounds about every 6 months as I gained more courage and acceptance to be honest with myself. I’ve reached a place where I don’t have to do huge purges anymore (except for jeans/pants, as you’ll see in the final installment). Now I’m refining, but it can still be hard, because the refinement process is where you tackle the hardest items to part with.

Today I’m taking you through my winter wardrobe and showing you what I’m getting rid of, why, and what I replaced it with. I also share some of the guilt and hard emotions attached to letting go and why I’m able to do it.

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my big ticket fail

A few years ago I fixated on buying the PERFECT trench coat. Nevermind I’d never owned a trench coat before, I suddenly decided I needed one, and it needed to be THE ONE. I researched and read and shopped and tried on. This went on for months. I wanted it for my birthday, but my true goal was to have it for our trip to AmsterdamBrugges, and France. I finally invested in one from Coach. It checked all the must-have boxes, and I thought I’d succeeded. Until. Until I realized that khaki (checkbox #1) looks AWFUL on me. Until I realized I hate double-breasted jackets (checkbox #2). Until I couldn’t stand to put it on, even when it would be perfect for my outfit. I was sick over it. I had invested in the perfect wardrobe must-have, and all the must-have reasons turned out to be what made them so wrong for me. I spent all that money, and now I wouldn’t wear it. I ended up selling it and getting most of my money back, but it took a while to admit the fail to myself, and even longer to take the steps to fix it.

why bother cleaning out your closet

Why bother with the flood of emotions and stress that can come with a closet purge? Because by releasing things that I don’t love, that don’t love me, that are in sad shape, or make me feel bad, I’m left only with the items I LOVE, the items I wear, the items that make me look and feel my very best. My goal with each purge is to be left with a wardrobe I love, and that loves me back by flattering my body and my skin tone. I’m left with a wardrobe that tells a true story about who I am, how I expect to be treated, and what you can expect from me. I’m left with clothes that make me feel confident, secure, and put together.

My closet is curated and cohesive, making getting dressed incredibly easy and fast. I can get ready in 20 minutes or less because my wardrobe isn’t full of a mishmash of random things that don’t go together. It all flows together to tell a story about me.

winter closet cleanout part 3 - scarves

winter closet cleanout part 4 - boots

winter closet cleanout part 5 - all the feelings

What items have you broken up with? What emotions have you experienced during a closet purge? What are you still holding onto, and why?

the quick and easy makeup tutorial i wore in these videos

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7 thoughts on “How To Deal With Guilt During A Winter Closet Cleanout”

  1. Thank you. I’m loving the videos. It’s helpful to me to hear your thought process and how you give specific reasons why something did or didn’t work for you. This is helping me see better what is and isn’t working for me. I purged my shirts a few days ago, after watching your first videos, and I was able to use my thinking mind more than my emotions to decide what to keep and what to let go of. This process is helping me to be more aware of specific things about an item rather than a vague “I don’t know, just don’t like it”.

  2. Jenni, I love this! I’m so so glad that these videos are helping you think through the WHY. Because if we don’t know why we get rid of something, we will buy…and purge another one just like it. I’m still identifying details of what I do and don’t like. I don’t like necklaces that have bulk on the side of my neck, so I don’t buy those anymore, no matter how cute they are.

  3. Your makeup video is great, can’t wait to watch the others. I so get the feeling of agonizing over the perfect item, and then realizing it’s not quite right. I lived as a DYT type 2 for about 3.5 years, so I had a pretty good sized wardrobe….one that made me feel really bad about myself. I realized last summer that I’m a type 4. I never fully got rid of my black–my armor! But it was hard to get rid of my type 2 investments. I ended up dumping a bunch in a ThredUp bag and shipping them off because I was expending too much mental energy on it!

  4. Cassandra, I’m not a DYT expert, but I bet those years as a T2 taught you things you needed, and maybe that will help you see that it was an investment in what you needed then. Good for you for sending it all to ThredUp and being done with the energy suck. Maybe I should do that. I still have a large portion of things I’m selling.

    I’m glad you liked the makeup video! I know a lot of us like to have one makeup look and wear it forever. I had the same makeup for….15 years. Brown shadow, brown liner, mascara, done. But now I’m really enjoying the experimentation process and changing my makeup to go with the seasons or my outfits. I’m not sure my audience is in the same mood, so it’s nice to hear it was helpful to you. Thanks.

  5. I really loved these videos and I’m looking forward to the remaining videos. I’ve lived with a minimal wardrobe & done lots of purging over the years…I’m good at purging…but I never really understood the why for what wasn’t working. I’m just now starting to identify why I love something/why something doesn’t work. I live with such a small wardrobe that my items all tend to die/wear out at the same time…then I become desperate for replacements…I’ll always get a few items right (thankfully) but I’ll get some wrong (of course…that happens when you don’t fully understand what is right and what is wrong.) Sadly, I wear the "wrong" stuff because I don’t have enough "right" stuff. (When you only have 6 shirts, you wear those 6 shirts. Lol.) My goal for 2019 is to work at this…shop around at least once a month…not just seasonally when I’m desperate. And if I find something I love…buy it. Anyways…all that babble & I really just wanted to share a tip for folks. I read a long time ago that holding on to clothes that make you feel bad about yourself makes you start your day feeling defeated. Even if it’s a subconscious thing…the visual of clothes that don’t fit/flatter properly in the closet or drawers is mentally depressing and hammers at your self-esteem. That really spoke to me & was the catalyst I needed to purge. So now I keep 2 nice shopping bags in my closet. If I try something on in the am & I take it off because I don’t like it, that item immediately goes into one of the bags. (One bag for donation, one bag for selling…depends on quality of item…if it’s worn past it’s useful life, I’ll trash it.) When the donation bag is full, I drop it off. I do not go through the donation bag again. I do go through the sell bag again when I have time to list the items. Only twice in 10 years have I pulled something out & tried to reintegrate it into my wardrobe. One item went back to the sell pile in just a few weeks. The other item is a light scarf…so we’ll see this Spring if it survives. There are 2 exceptions for rehanging vs. bagging: 1. If it’s a color match or silhouette thing. I like the items…but the outfit didn’t go together as I imagined. OR 2. If it’s because the outfit wasn’t the right level of dress for the occasion. Other than that, I’ve learned that if I don’t like it today (fit, style, material, whatever) I’m not going to like it two weeks from now on a Thursday. And my final tip is a note on perspective. Although I know it’s common, nobody should feel guilt over this process. The worst guilt of all is "unearned" guilt…and anything related to disposing of an item that no longer works for them is definitely unearned guilt. When I’m feeling "guilty" over something, I’ll ask myself "is this unearned guilt?" If the answer is yes, it’s much easier to let something go. I’ve also gotten pretty good at this practice over the years & it has released a lot of stress in my life.

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