Week 5 of the 2016 Clever Girl Organizing Challenge: All the Clothes, Week 2

It’s Week 5.  First, a shout out:  You’re more than 25% done with The Challenge!  Hooray!  High Fives for Everyone!

Okay, now, that we got that out of the way, let’s get down to business. This is the week we dive into your clothes. This is going to be a lengthier post, because there are the guidelines about how to think about your clothes, and then the assignment levels themselves. So, stay with me.  

Now, if you also want to take this to other people’s closets in your home (if you have full authority and decision-making power of those wardrobes), that also works, but it’s really to start with YOU and YOUR clothes.  Closets, dressers, wardrobes, under bed boxes, wherever you have your wardrobe stored.  Accessories, socks, underwear, outer wear and shoes are next week, by the way.

I want to start by getting you thinking about your clothes, what you may have in your collection, and how to start thinking about it differently going forward. I’ve got a list of 5 questions you’ll be asking yourself about your clothes, as guidelines on what to keep, and what to let go of now. As you go through your clothes, you’re going to scrutinize everything, and make commitments to keep only the items that pass all 5 questions.   But before we jump in, let’s assume the basics about the clothes you’re even considering keeping:

  • The clothes fit you now, or are one size up or down, and a realistic fit for the near future (let’s say “near” is the next year or so).  Sizes outside of that range should either be donated (top choice) or bagged/boxed up and put somewhere else, so they are not getting in the way of you having a fully functioning wardrobe and choices each day. Let’s face it – if you REALLY end up being 2 or more sizes off from where you are today, you’ll end up getting new clothes that work for you then. If you’ve *finally* lost the weight you’d been saying you were going to lose for a while, won’t you want to make sure you’re wearing things that you love, that are in your current style and tastes?  That may not be the items lurking in your closet now.  
  • They are not stained, ripped, damaged or faded (unless they’re clothes you set aside for things like painting days or lawn mowing, and you really only need one or two sets of clothes in this category.)


Here are the questions to ask yourself about each item, and some qualifiers so you know what I mean. And while the language might sound that it’s more geared to women, please, guys, we know you care about how you look, too.  These rules apply to everyone. 
Top 5 Wardrobe Review Rules

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 on the street while wearing it, you’d feel totally fine about being seen in it.

2. Does it love you back?

  • It flatters your current shape.
  • 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 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 life style?

  • 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 a “I can wear this to a wedding” item, is it one you WILL wear, or 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?
    • Work clothing — especially suits — do you wear suits now? Is it highly likely you’ll wear them in the future?  If yes, are THESE the suits you’ll wear at that time? 
    • 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 sleep wear? 
  • 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?

  • 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. Could someone else get more use out of it in the future than you really will?

  • 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.  And so on, and so on, and so on.


Okay, so, those are my 5 rules. Notice I didn’t mention the “haven’t worn it in xx months or years” rule that many people will use.  You should if it means something to you. For me, I think the above reasons lead to WHY you haven’t worn it in xx months, and I’m all about the WHY.   But it’s a good question to ask yourself to get to the “so, why is that?” follow-up. 

I hope they made sense and that the examples I gave brought some things to life for you.   Now, let’s get into this week’s assignment:


16 challenge 


Week 5: Tackle Your Wardrobe!

Level 1 Challenge: Review and clean out your closets, dressers, wardrobes, armoires, under bed boxes, or wherever you store your clothing. Get in there and get this tackled, but remember, this one is an “it gets worse before it gets better” kind of assignment, as we start to dive in.  You’re going to want to touch all the clothes, and remember, we’re focusing on “Do I Have A Good Reason To Keep This?” instead of than the Status Quo “Do I Have A Good Reason To Let Go Of It?” Every piece of clothing needs to make a case for staying, and that’s what the 5 rules are about. Be critical. Remember — you’re reclaiming some of the most important storage space in your home, and you want it for the things you LOVE and NEED. 

How to tackle this one:  Well, the rules above are just guidelines. You also need a STRATEGY of attack. A few things to keep in mind:

  • You’ll need some space to work.  Make your bed before starting, and work with that as a surface. You may work with cleared out spots on the floor, too. Do what works, but start with working space.
  • Have bags for donate (for good items), recycle (for items that can probably only be salvaged for textiles) ready to go. You may also want a box or bag for “sell or consign”, “needs mending” and, the all important “belongs somewhere else”, which always seems to pop up in this challenge, doesn’t it?
  • Set up music, and make sure you have a decent amount of time to set aside to this project. You can definitely break it into multiple sessions, if you plan for this.  You don’t want to get burned out, though, so manage your time and energy for success.
  • There are AT LEAST 2 ways to start:  By Zone or By Category.  By Zone would say, “I’m going through the dresser first. I’m starting with the top drawer, and will do each drawer before moving onto the next one.”  By Category would say, “I’m working on all the pants first, regardless of whether they’re stored together or not.”  Honestly, I prefer the category approach, because it allows you to truly see all the items you have in a particular group, and sometimes, when you see them all together, you see the whole story:  “I have more than I thought I did, or need in this category” is a common discovery. 
  • You may have to try things on; don’t just rely on the last time you wore it, if it’s one of those items that has lingered in your closet for a while, but you’re still leaning towards keeping it. Now, this can be tricky.  Do you do it immediately, or save to the end, with other things to try on?   If it’s something you can do in 2 minutes or less, try it on now.  If you think there is really going to be a number of things to try on, and you feel you can still make decisions about OTHER things and that won’t hold you up, you can set items aside for a final try-on round. 
  • You may already know where things are going back to when they’re weeded down, but you may not. Remember my strategy post last week about perfection:  Don’t let the fact that you imagine that there *must be a better way* to organize this prevent you from putting things back when you’re done. You won’t want to live in “waiting for the perfect solution” chaos, and it won’t motivate you to get it done any quicker once you get used to the chaos. 
  • Get the clothes for donation out of your home as quickly as you can… either put them in your car to drop them off, or schedule that pick up from your favorite charity ASAP. 
  • Don’t forget the BEFORE pictures!  I promise, you’re going to want these! 

A final warning.  Here’s a dangerous one that comes up.  “I paid a lot of money for this.” This is called a sunk-cost attachment, where your reason for holding on to something is directly related to the decision-making you made on the day you acquired it, regardless of the value it currently holds in your life. This is going to come up in several challenges (it may already have in the kitchen).  Here is what I’d like you to consider:  If you have a shirt that you got for $10 and you wear it all the time, it has more value in your life (value for clothes = wearability) than the $70 shirt (splurge) you thought you’d wear but never did.  In fact, that $70 shirt has a NEGATIVE value in your life, because not only is the shirt not contributing to your life as a wearable shirt, it’s also taking up valuable space from one that could, or just space that doesn’t have to be filled at all. 

Level 2: Review the wardrobes of anyone else in the home for whom you have total decision-making authority, or team up with them together if you don’t.  Same thing as above, but elsewhere… your kids rooms, your spouse’s clothes, whatever awaits.  For young kids, you likely have full authority. For tweens and teens, it’s a good opportunity to work together, and help them with their critical thinking and decision-making skills. These kinds of activities are core for executive functioning (skills like sorting, categorizing, critical thinking, time management, prioritization, and focus), and you can work together to help promote that development, while also helping promote a clean and organized closet!  For spouses, you probably don’t have authority, but if you have permission to do a pre-review — gathering items together from the same category, for instance, and your spouse agrees that s/he WANTS to do this assignment, perhaps that’s one way to work together – you do the leg work, s/he does the decision-making, and you move forward. 

(If you already have conquered your wardrobe, or you don’t have anyone else in the home to work with, you can make up an independent study task!) 

How The Challenge Works:
As With Every Week, Your mission:

1) Take on Level 1, and if you’re feeling up to the challenge, Level 2. If you’ve already got those covered, identify a challenge for yourself that you know you should be tackling.

2) Whenever possible, take BEFORE and AFTER pictures. You don’t have to share them with anyone but yourself, but it is a fantastic way to (a) identify clutter that’s become invisible to you over time and (b) truly measure and appreciate your progress. 

3) We’re all about letting things go…  be critical about what you’re keeping and why you’re keeping it.  Always ask yourself these critical questions to help decide if you should hold onto items: 

  • Is using this item part of my current life or likely future?
  • If I didn’t have this item and needed it for some reason, is it easily replaced or borrowed?
  • Can someone else use this more than I seem to be using it now? 
  • Am I keeping it for a “maybe some day” or a “just in case” option? How likely is that situation? And am I keeping more in that category than I should, given the space constraints I have?
  • Is it part of my past, and holding onto it reminds me of a former self? And am I keeping more in that category than I should, given the space constraints I have?

4) Stay FOCUSED on this task.  Know what FINISHED looks like, and don’t get distracted by other projects or areas of attention that cross your path while you’re on this assignment.  

5) Have a plan on where things will go — give away to someone you know, donate, sell, recycle or trash.  This Challenge isn’t just about creating new piles that don’t have a future!

6) Work in manageable chunks of time and energy. It’s a marathon, not a sprint! 

7) Celebrate and reward yourself for a job well done!



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