Year End Tax Planning: A (Surprising) System of Cleaning My Closet

On the way home from this Thanksgiving weekend in Michigan, I finally reached my limit with the situation in my closet.

For the last four years it’s become bigger and bigger mounds of….clothing. Just as I get the closet organized, it becomes a mess yet again. Being a recovering financial advisor, I loathe messes. Everything should be in neat and tidy rows, not thrown on the closet floor.

Historically, at this point I’d decide to get rid of clothing. I’d pick up stuff and make the “stow or go” draft move:

“No,” the hoarder in me said, “I’ll wear that some day.”

“I got that at my favorite 5k in 1998. I can’t get rid of the Pickle Run shirt!”

“If I get that stain out I’d wear it all over the place.”

I should have been saying, “Some day bell bottoms will come back in style!”

Sometimes–not often enough–I’d find a piece that definitely had to go. Whenever I brought home new clothing from holidays or trips to the mall, old stuff stacked up. The “donation” pile contained a lonely piece or two. I was adding clothing at a 2:1 rate over donations.

On the way home I snapped. Suddenly I formulated a plan:


The Plan


It was so easy, I can’t believe I hadn’t seen it earlier.

Clothing decisions (and by extension “stuff” in general”) isn’t about whether I like each “thing” or not; of course I loved them all. I wouldn’t have bought them if I didn’t like them. They all had sentimental value AND my mind needed to justify the reason I’d added them to my collection in the first place.

In short: using my current criteria, there was no way I’d ever clean out the closet.

In my a-ha moment, I flipped my thinking: the closet wasn’t a place to store all the cool stuff I wanted to keep. It was a place to store things I needed.

Following that train of thought led me to the real question:

How much did I really need?


The List


I made a list of things I really needed:

10 Long Sleeve Running Shirts (probably don’t need 10, but that was a start)

10 Short Sleeve Running Shirts (closer to the number)

4 Pairs Running Shorts

3 Pairs of Jeans

4 Pairs of Dress Pants

3 Suits (again, probably too many for my lifestyle, but I could cut more later)

6 Ties

6 Button down shirts

5 Pullover sweaters

….and so on.


…and Action!


Sunday was a bloodbath in my closet. I tore everything out and placed it on the floor. I was making Top 10 lists of each type of clothing. Soon I was at the difficult portion: there were pieces I liked, but they didn’t make the  Top 10 (or 5, or whatever….). At this point it didn’t matter how much I liked the shirt: there were enough pieces for me to wear without it in my closet. Better to gift it to someone who really needs it this holiday than to keep it sitting in my closet with 10+ items I’d rather wear.

I created a gigantic mound of clothing to donate.


Itemized Charitable Donation Deductions: Bonus Time!


If you itemize your taxes, you are probably eligible for charitable donations to 501c3 organizations. If you aren’t sure whether the place you want to donate clothing is a 501c3, just ask them. They’ll know.

If your organization is eligible and you itemize deductions on your taxes, you may be able to write off your charitable contributions. I received a receipt at Goodwill that listed all of the items I’d donated to them. I’ll use this at tax time next year.



The Lesson


I’ve learned this lesson 100 times and still continue to struggle with it daily. Don’t get caught in one line of thinking about a problem….especially nagging ones like cleaning out a closet. Turn the question around. Search for a better answer. Scour the web for strategies….soon you’ll have a clean closet, better decisions and possibly tax deductions!


This is another in our list of systems for busy people. Want more? Check out our budget plan for busy couples. It’s another play-tested system (that one OG uses with couples all the time and I used when practicing…it’s worked magic for non-budgeters.)

What are you waiting for? Go clean out that closet and cha-ching on the tax deductions!!!! What system do you use for weeding out old clothes you still love but should probably chuck?

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  1. says

    Good for you! My wife has been trying to make me clean out the crab I haven’t worn in years but I keep fighting it. Even though you will be giving clothes away you will have a better ability to know exactly what you are missing and only buy it and clothes you don’t need.
    Jon recently posted..Smarterbanks ReviewMy Profile

  2. says

    I generally dislike going clothes shopping, so it’s usually the clothes that decide when it’s time to make their departure. They let me know by fraying at the edges or getting more holes than is socially acceptable anywhere other than a grunge concert.

    But there are definitely a couple pieces that I patch and keep around because I like them and I like being able to know that I can still fit into something I bought when I was 14!
    Mrs. Pop @ Planting Our Pennies recently posted..He Said, She Said – Buying A $2K AmpMy Profile

    • Average Joe says

      I can fit into stuff I bought when I was 14….but they look like a halter top and short-shorts. Not great on a 40 something year old dude….

  3. says

    More power to you on cleaning out the closet…It takes a mood to tackle that…I share a big closet with my kids so my wife just puts my stuff in the back…so its outta sight outta mind…Sometimes as in all of life we do get into a one track mindset of going about a problem and exploring outside of our comfort zone may be hard …
    Christopher @ This that and the MBA recently posted..3 Steps to Eliminate Procrastination I Actually Learned In SchoolMy Profile

  4. says

    I am the exact same way! Why is it that I am a hard core planner, I like things nice & neat and in their place, BUT my closet looks like something exploded in it? I’ve gone through it a few times but your list idea is one I need to seriously look at. Not only to be more organized, but I think it’ll also win me more than a few brownie points with my wife. :)
    John S @ Frugal Rules recently posted..Why Rebalancing Your Portfolio is Like Buying a Carton of EggsMy Profile

  5. says

    You tackled a big job, that is best done this time of year, when others need so much.

    My husband and I share a walk in closet and he has more dress clothes than I do from his days of working in a corporate office. So many of his dress shirts are covered in dust but are brand new and not something that goes out of style. We have these large plastic vacuum bags and I was thinking the other day that we should wash all of his shirts and put 90% of them in those bags to store them better.
    Tackling Our Debt recently posted..Six Benefits of Starting Your Own BusinessMy Profile

  6. says

    I love doing this! Need to get on the ball and clean out my dresser because it’s busting at the seams with old t-shirts I’ll never wear, and my closet is half full of old suits from when I worked in public accounting. Seems a shame to get rid of them while I can still fit into them, but maybe I can find a local charity that takes interview outfits.

    How do you keep track of donations? I’ve been using It’s Deductible (free online) and I love it because it keeps records from past years and you can enter items as you have time and return later to finish.
    Lena @ WhatMommyDoes recently posted..What is a Pantry or Fridge Challenge?My Profile

    • Average Joe says

      I WAS THAT GUY! D and I might be twins. Shirts I loved with a hole or a stain couldn’t leave my closet….but finally I got rid of them.

    • Average Joe says

      That’s a great rule! I would have sworn up and down that I’d worn it in the last two years. Then if my mother didn’t believe me, I would have worn it that day.

  7. says

    I have a few sentimental items similar to the Pickle Run shirt, like the Country Ham Jam and all my Turkey Trot T-shirts, but I am pretty good at getting rid of stuff. My husband is a different story. I have to pull out items very slowly so he doesn’t miss them. He would keep everything until the door blew off the hinges.
    Kim@Eyesonthedollar recently posted..Do Your Purchases Reflect Your Values?My Profile

  8. says

    I’m pretty good about what I keep and what I get rid of. The Mrs. on the other hand is miserable when it comes to cleaning out the closet. She literally uses all the closets in our bedroom to stash something or other including clothing. Little by little we get rid of stuff but trying to tear a woman away from their clothes is tough stuff… Thanks for sharing mate. Mr.CBB
    Canadian Budget Binder recently posted..CBB Net Worth Update~November 2012My Profile

    • Average Joe says

      That’s Cheryl and her books. She’s promised me about a gazillion times (rounding down) that she’ll donate some of the books she’s read. Not yet.

  9. says

    You sound like me – “Uh oh, it’s December! Better donate stuff!”.

    If only I had done it earlier in the year it wouldn’t be such a rush, eh? Anyway, we tend to split our donations between the Salvation Army (I even gave them a car once, haha) and Goodwill.
    PK recently posted..Wealth is Not IncomeMy Profile

    • Average Joe says

      I gave a car once, too! It was far cheaper than the towing and fix-it job that was going to have to happen otherwise.

  10. says

    I love this! It is not very often that I think ‘I wish I thought about this first’ but I am thinking it now. Will apply immediately (well, not tomorrow but next weekend). And your reasoning at the start made me laugh – I do exactly the same, and use identical wording (including these being about race shirts of which I have about 50).
    maria@moneyprinciple recently posted..How do you feel about Christmas? Honestly?My Profile

    • Average Joe says

      I love that advice, Elizabeth, about not opening boxes in the attic. If you’ve lived without them for this long, just donate them unopened.

  11. says

    Dear Average,
    I liked what you said about Clothing decisions (and by extension “stuff” in general”) isn’t about whether I like each “thing” or not; of course I loved them all. I wouldn’t have bought them if I didn’t like them. They all had sentimental value AND my mind needed to justify the reason I’d added them to my collection in the first place.
    Continue this kind of articles because they are very good and useful, congratulations.
    Income Tax recently posted..Ways Of Choosing The Right Edmonton AccountantMy Profile


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