Week 5 – The CLOTHES!

It’s Week 5 of the 2022 Clever Girl Organizing Challenge! We’re rolling off our first BREAK week and DIVING into an area that most people need to pay attention to, whether they’ve done The Challenge before or not. Why? Life evolves. Bodies evolve. Needs and tastes evolve.

This week, the focus on clothing and accessories for you and for anyone else in the house for whom you are primarily responsible for wardrobe maintenance or anyone you can INSPIRE to work with you on their own wardrobes. (or, just focus on you, if that’s plenty!)

I know that everyone has some anxiety about this topic… I do, too! But I also want you to focus on the BENEFIT of going through your wardrobes. There are the obvious outcomes like your closet doors closing again, your dressers drawers closing more easily, being able to find what you’re looking for when you need it, more easily putting away your clean laundry, saving time, and saving money when your clothes are taken care of (or not lost or forgotten about and then replaced).

But what’s really in store for you: Knowing that what’s in your wardrobe is EARNING its spot there. It absolutely works with you and your life, and your wardrobe is a tool that SERVES you, doesn’t drag you down and make you feel bad about yourself. Remember, we’re here to make our lives BETTER through decluttering and organizing!

Don’t forget the two guidelines I’d love for you to keep in mind before you start your work:

1) Have the tools you need before you get started — trash bags, recycling, donate box, and “goes somewhere else” box (so you can set things aside and keep going, not be tempted to return things to a different space while you’re working).

2) Keep up on that BEFORE and AFTER picture taking! I see people saying “Shoot! I forgot to take a before picture” and then they know they’re missing out on expressing to everyone just how tremendous their transformation was. 🙂



So, what are the categories and spaces you might consider this week to tackle? Remember, you don’t need to do ALL of this! I want to give you ideas of where your time might be best spent, based on YOUR needs in YOUR space. Think about what you have, what you know you haven’t looked at in a while or what you know causes some strain on your storage systems. Most importantly, think of who you are, your current and foreseeable lifestyle, and what items just don’t align with that any more (if they ever did)!

Now, we clearly need to talk about the pandemic-year(s) impact on our consideration. If you’re the kind of person who would normally say, “If I haven’t worn it in 6 months, it should go,” well, this year may not be the measuring stick you want to use. BUT, in some ways, the pandemic-year impact can actually be a great deal of clarity. We’re much further from the days where something that felt like a “maybe” could be more of a “no” now. A year ago, you might have said, “Well, let’s see what the coming year brings,” and now you’re able to say, “let’s face it… I don’t WANT the kind of life in the future that’s going to make THIS a keeper anymore.”

As you begin this week, I want to ground you with 2 sets of concepts to think about. The first is “what may creep up” and cause you to hold onto things even when you know logically you should consider letting it go. I have a ton of these triggers to watch out for in the “Why is this so hard” section below, so be sure to sit with it a bit.

The second is a set of 5 questions you can ask yourself about any individual piece of clothing to help you determine if it’s a candidate to stay. Notice I said: If it’s a candidate to STAY, not is it a candidate to GO. That’s because I believe this process gives you an opportunity in which you have to develop good and strong reasons for something to stay, not just find reasons to part with something. Everything needs to defend its own existence in order to stay in your wardrobe! aLet’s explore these practical questions you can ask yourself about individual items to help you through the process. Hint: You’re looking for 5 yeses for each item.

1. Do you love it?

  • You love how you look when you wear it.
  • You feel good when you wear it.
  • When you think of something you want to wear on any given day, it’s high in the rotation.
  • When you put it on, you tend to keep it on, rather than change your mind for something else and take it off.
  • If you ran into an ex or your boss on the street while wearing it, you’d feel totally fine about being seen in it.

2. Does it love you back?

  • It definitely fits.
  • It flatters your current shape.
  • It’s in great shape — no tears, no faded spots, no stains, etc.
  • The color works with your complexion.
  • It doesn’t itch or have scratchy seams.
  • It feels comfortable when you sit, stand or walk while wearing it. You don’t fuss with it or tug at it.
  • You feel comfortable with the neckline/waist height/sleeve length, etc. You are not self-conscious about any part of it.
  • You don’t get distracted by it during the day when you’re wearing it, wondering if it’s still fitting the right way.

3. Does it fit your current and foreseeable lifestyle?

  • It fits into your normal current lifestyle (work clothing appropriate for your current job, casual clothing, or special occasions that are likely to occur). Some questions to figure that out:
    • Special occasion clothing – if it is an “I can wear this to a wedding” item, is it one you WILL wear, or just one you COULD wear? Do you tend to wear repeats, or shop for something new each time?
    • Special occasion clothing – “This is good for a holiday party” — how often do you normally attend these types of parties, and is it likely you’ll wear this item at that time? And what would you do if you didn’t own this item anymore and a holiday party came about?
    • Work clothing — especially suits and blazers — do you wear these now? Is it highly likely you’ll wear them in the future? If yes, are THESE the pieces you’ll wear at that time? (Mens dress shirts — too many shirts, all slightly different shades of blue?)
    • Workout clothing/Sports/activity gear — we all have clothes that may fall in the workout category or be special for different activities. Does the supply of what you have really match the amount of occasions you have to wear them? Are you holding onto some of these pieces due to ASPIRATION?
    • Casual clothing — do you have a lifestyle that you have enough opportunity to wear the casual clothing you have collected? (example: 8 great skiing sweaters, but you only go skiing one or two times a year?)
    • REALLY casual clothing — Have you put it in the “I could sleep in this” or “I could paint in this” or “I could mow the lawn in this” pile? If so, have you demoted the items that have been in those piles longer? Do you really paint and mow that much? Do you need a dozen options for sleepwear?
  • You have the right amount of what you need for core items (example: jeans, black pants, solid white or blue dress shirts, workout clothes, etc.). If you wear black pants every day, what is the realistic amount to have on hand, and how does that compare to the size of your collection? If your collection is greater, how do you prioritize on any given day what you choose to wear? That’s how you should prioritize to choose to keep the necessary amount.
  • Is the care required more than your lifestyle can handle? It’s dry clean only, or hand wash, or some other such craziness that just isn’t part of your life right now. All the hand-wash-only and dry-clean-only items end up in a pile, worn once, wrinkled, left to die a lonely death of cashmere and sequins and linen.

4. If you went shopping today, would you pick it out and buy it?

  • You’ve heard me use this one before, and it’s never more relevant than with clothing. If you wouldn’t pick it out to buy today, why do you think you’d actually wear this tomorrow? Sure, we all have clothes that we bought when we were shopping for something (or nothing) in particular, some time ago. It may just as well have served its purpose in our life, and if it’s not something you’d make the same choice to take home today, why are you KEEPING it in your home?

5. Am I REALLY getting more use out of it than someone else would?

  • Sure, it’s a good piece, and it looks good on you, and you like it enough, and you might have occasion to wear it. But, is it really being valued in your closet? Could someone else use it and love it so much that it is the top of their list?
  • Winter coats come to mind on this one, for instance. You have several perfectly great coats. You don’t need them all. Someone else really, really, really needs one, and would be grateful for yours. Or business suits for people who don’t have good clothing to wear to job interviews. Or shoes, especially those fancy, “good” shoes. And so on, and so on, and so on.

Okay, so, those are my 5 questions, and again, none of these are “if you haven’t worn them in xx months, let them go.” This was already NOT a rule I recommended pre-covid. But it’s a good question to ask yourself to get to the “so, why is that?” follow-up.

Finally – a note about different sizes. We all struggle with weight fluctuation, and keeping SOME items in “neighboring” sizes makes some sense. That doesn’t mean these have to be STORED with your regular wardrobe. Put limits on this category, and come up with a storage solution that doesn’t invite these pieces to get in the way of your daily choices of what to wear.

I want you to figure out your lifestyle and what is reasonable, and the amount of space you have in your home that you’re willing to comfortably allocate to store clothes, knowing you can’t use that space for something else if you do. I know this week’s “Why is this so hard” is a meaty one. You may need a while to absorb it before jumping in to do the work. But don’t wait too long to jump! 🙂


Remember, you’re making decisions based on the value the items play to you in your current and foreseeable future and recognizing that anything else is probably clutter, and clutter is getting in your way of using your home the way you want to. This is why we’re doing this work; to cut down on the cost of clutter in our lives. 


Each week, we have 3 levels for you to engage in. Pick the one that feels like it will work with your time, energy, and needs for the week. You can always rally later in the week and do more! If you’re managing your time closely and can’t do a lot in one session, see what you can do in a 20-Minute Attack. Set a timer, stay focused, and see what you can accomplish in less time than it would take to watch a sitcom! And let us know what you path you’re on each week with the hashtag #tackleit and then the week we’re on, for example: #tackleit  #week5

All Aboard (This is the normal challenge level):

–  Tops – shirts, sweaters, t-shirts, sweatshirts, etc.
– Pants – trousers, leggings, jeans, etc.
– Dresses, Suits, Businesswear
– Workout wear
– Shoes — athletic, casual, business, special occasion, flip flops, crocs, hiking, boots, etc.
– Formal wear/Party Clothing
– Socks
– Underwear
– Outerwear – coats, jackets, etc.
– Accessories — scarves, belts, costume jewelry, baseball hats, etc.
– Clean your night table OR the surface of your dresser

MiniChallenge (for people with limited time or energy this week)

– One full category of tops (t-shirts OR sweaters, for instance)
– One full category of pants
– Two full category of shoes
– One full category of accessories or socks/underwear

LevelUp Challenge (for people with more time, energy, or greater need)
In addition to the All Aboard Challenge: 
– Clean off the surfaces in your bedroom — night tables, dressers, etc.


I’ll make some videos during the week about FOLDING and HANGING different clothing types as tools and I will post them in the Facebook Group. Any requests?? Let me know! 



Our wardrobes (and those of others in the house that we’re primarily responsible for) can have a tangle of emotions wrapped up in so many items. Some of these we’ve talked about already, but a few need some deeper dive. I want you to listen for these “reasons” you’ll hear yourself come up with to hold on to something. Here are some that come to mind right off the bat, and we’ve already started talking about some of these in the Weekly Facebook Live conversations, so some of this will be reinforcement. 


1) Sunk Cost: “I paid good money for this” or “This was expensive”

Sunk cost is the principle that you’re sticking with a plan because you’ve ALREADY paid money or invested in it. You’re evaluating an item based on how much you’ve already paid for it in the past. The first news is the harsh reality: Holding onto the item will NOT bring you back that money. (Sure, you might be able to sell it, but chances are, if you’re stuck on an item because of sunk cost, you’re not even thinking about selling it). What I want you to think of instead of COST is the VALUE of an item. You could have a shirt that you spent $20 on at Target, one you wear every week year-round, hanging next to a gorgeous top from Nordstrom that you spent $150 that you never wear or you wore once, 3 years ago. The item that actually has more VALUE to you is the Target shirt. Think to yourself what holding onto the Nordstrom shirt is really GIVING you and the quality of your life and future. Probably not much; it’s merely become the representative of a decision you made a long time ago that wasn’t a winner, and you’re holding on to it to see if there will ever come a time in the future where past-you, the one that made the decision to buy, will be proven right.

Another part of the sunk cost world is The Curse of the Bargain Shopper. It probably wasn’t something you were planning on getting or specifically looking for, but it shows itself: THE OPPORTUNITY. Here’s how it plays out:

  • You found something on sale or something that was just a great bargain. This is the first dopamine hit your brain got: “Look! I’ve tricked the universe, I’ve got one-up on the retail gods. I found this GREAT deal on this thing.” = VICTORY ACHIEVEMENT
  • Then, you tell yourself, “Well, even if I don’t love it, it’s such a bargain that it isn’t a big loss if I don’t wear it often” = RISK MINIMIZER
  • You’ll convince yourself, “And if I don’t love it, I can always return it” = THE “NO COMMITMENT” MYTH
  • And, finally, because it wasn’t something you were specifically looking for that day, it sits, ignored for a while, until one day you see it, remember it, and revisit it. Because all the other convincing has faded, you now see the item in a new light. And you don’t love it. And it’s been too long to return it (or you lost the receipt), or you just say, “eh, it wasn’t a lot of money; it’s not worth the trip to go back.)
  • From there, it either stays in the “Maybe I’ll magically fall in love with it again someday” pile (because you feel guilty that you wasted money on it) or it goes in the donation pile, tags still on.

You know this story, I’m sure, for at least one item in your life. If this is you, I want you to recognize these triggers and habits that are going on for you in the SPORT of shopping.

2) Guilt: “It was a gift” or “It was Retail Therapy”

Sometimes, we hold onto something we really don’t like because we’d feel *guilty* if we let it go. The emotion that’s really here is “I don’t want to hurt anyone else’s feelings, so I’ll just hold onto it because that’s less punishment than the feeling of hurting someone.” You’re willing to suffer so you don’t hurt someone else. I get it; it’s admirable. But if we’re in your closet, we’re talking about shirts and pants here; these are not relationship-altering decisions. Anyone who liked you enough to give you a shirt doesn’t want you to feel like it is making you suffer.

The tricky one that comes up: “My husband bought me this because he liked it but I just don’t wear it… and I don’t want to hurt his feelings.” Again, I’m going to remind you that your husband’s goal in buying you something was not to burden you with guilt and negative feelings. Maybe he’s bad at giving gifts. Maybe he would love to see you change things up in your wardrobe and thought this could be a way to do it. I don’t know. I do know that, deep down, he doesn’t want you to hate something you own and hold onto it just because you love him.

Retail Therapy — shopping felt good, buying felt good… even *owning* feels good. But it’s an item that’s wrapped up in the “feel good” emotions, not one that’s actually a practical part of your life. And so, there is some guilt because you know the tug of war going on between “this isn’t what I want my home to feel like” and, ironically, “but shopping makes me feel good when I’m feeling this way.” 

3) Purposeless Possession: “But this is still good”

You will come across items that you don’t wear, but you will be inclined to hold onto because “this is still good“. You say it, and you stop thinking about things like “Yeah, but do I wear it? WILL I wear it?” When something is still in good shape, we feel like we don’t have permission to let it go. I’m here to tell you: YOU DO!

One of the categories we’ll see this happen is going to be in that “fancy” wear — our party clothes, outfits we wore to weddings (or bought for a possible wedding someday), our “good” and event shoes. This is really where we triangulate among the different factors:
– do I have enough space such that storing these mean I’m not sacrificing in anyway
– am I holding onto these because I will wear them again, or because I loved wearing them in the past?
– when it comes around to having an event again like this, will I definitely wear this, or will I want something new?

Another trap in this space as I mentioned above, is the demote-able items — for sleeping, painting, mowing, etc. We’re so hesitant to let go of something that we can invent new purposes for it. That’s fine, but unless you’re a professional painter, you probably only need 1 or 2 of those painting shirts. And chances are, you already have the sleepwear you love. Beware of creating big piles in these “rescue” categories.

4) Future Fear: “I might need it someday”.

This can be for items that are particularly unique — the cocktail dress, the costume, the suit, etc. — or it can be for that dreaded “other size” you’re afraid you might need again someday. That’s right; I’m talking about the clothes that don’t fit you, either the “but I might be 3 sizes smaller again someday” or the “but I might gain that weight back” clothes. In both cases, holding onto these can be about money (“I’d hate to have to spend money to have a new wardrobe if I ever get there again”) or about not enjoying shopping and feeling like holding onto your own “store” will rescue you from having to shopping again. When you’re in this space, holding onto items because you’re afraid that you might need them again in the future and will be somehow negatively impacted if that moment comes and this item didn’t exist anymore, you’re also trying to protect yourself from that feeling of, “Shoot! I totally used to have something that would work and I got rid of it! i’m so stupid!“. REGRET, amiright?

There are even more that will come up, I’m sure, and I look forward to having these discussions in the Facebook Group this week or on the ZOOM LIVE on Thursday night at 8pm Eastern — where we all get to talk “face to face” 🙂 

    Remember: You’re here because you made a choice to bring your head, heart, and body all in the same direction: to let go of things and have smoother systems in your home. If it was easy, you’d be done by now.





    I have work to do in this space too! I look forward to diving in there with you all! 


     Happy Organizing!








    THURSDAY, FEBRUARY 3  – 8:00pm Eastern



    missed the last one? Click here.  






    Week 1 – Jan 3: Kitchen: Food – Pantry, Fridge, and Freezer
    Week 2 – Jan 10: Kitchen/Dining: What we use to prep, cook, serve, eat, store, and clean after eating! 
    Week 3 – Jan 17: Bath and Bed: Medicines, Toiletries, Cosmetics, Personal Items, etc. 
    Week 4 – Jan 24: BREAK – take a break, catch up, or sneak ahead
    Week 5 – Jan 31: Clothes, shoes, accessories
    Week 6 – Feb 7: Living / Family Room spaces
    Week 7 – Feb 14: Kid stuff / Holiday Decor / Pet stuff (Choose Your Own Adventure)
    Week 8 – Feb 21: BREAK – take a break, catch up, or sneak ahead
    Week 9 – Feb 28: Memorabilia
    Week 10 – Mar 7: Home Office/Papers
    Week 11 – Mar 14: Hobbies / Arts and Crafts / Sporting Goods