The Well Dressed Life Wardrobe Challenge 2021: Week 3

Four Weeks to a Better Wardrobe - Week 3 - The Well Dressed Life4 Weeks to a Better Wardrobe: Step 3

This week’s challenge is all about getting your space organized! I am a big believer in organization. It makes life easier, saves money, and allows you to manage your time and energy better.

I worked with private clients for over a decade. I know this for sure: a messy, unorganized closet space is one of the biggest reasons women feel overwhelmed (or underwhelmed) by their wardrobes. The good news is it’s the easiest issue to fix.

And remember to join me today at 3 PM EST for our LIVE chat in our Private Facebook group – we’ll recap last week and set you up for the next round of challenges. 

Week 3: Getting Organized

Your closet space should be lovely or, at the very least, tidy. It should bring a sense of calm, not craziness. It doesn’t matter what kind of closet you have. You could have a huge, custom walk-in or a simple bar and shelf. Either way, your experience can be blissful.

Challenge #1: Finish your edit

Last week, I challenged you to perform a QUICK edit. This is my clever way of easing you into a more in-depth edit, especially if you have a hard time letting go of things or have a lot of stuff. 

If you still have an undecided pile, now is the time to be ruthless. Get rid of anything you don’t love or need. Be honest with yourself.

Are you going to wear it?

The only exception is if you NEED to wear the piece until you replace it with a better version. Make a note of it. You’ll need it next week when we create a shopping list.

If you are on a weight loss journey and have some pieces that don’t fit well, you can keep them, but remove them from your closet and store them elsewhere.

I don’t want you waking up to a closet full of clothes that don’t fit. It’s not a great way to start your day.

Be sure the items you decide to keep are modern, fit your style, and are things that you look forward to wearing when you hit your goals.

If a piece is sentimental, give it the respect it deserves. Have it professionally cleaned, remove it from the plastic dry-cleaning bag, wrap it in acid-free tissue, and store it with the rest of your keepsakes. 

I love these cedar trunks. I have one for each of my girls and myself and store special pieces that are either memories or garments I want my kids to have when they get older.

Challenge #2: Improve Organization

Take some time to find a place for everything. I know, I know; this was supposed to be fun!

I promise that an organized and clean space will help with your creativity. The process of creating outfits will not seem so daunting when you see what you have. A few quick tips:

Remove everything from your closet.

Give it a quick clean. I have seen enough closets in my day to know you have pieces hidden in the back, covered in dust. Dust will destroy your clothes. Take 15 minutes to wipe off your shelves, vacuum, throw away old hangers and miscellaneous items.

Only put back your wardrobe.

I once found a toaster in a client’s closet that she’d forgotten she’d bought. Find another place for everything else (if you can). Remember to keep your Pinterest board close by so that you can continue to use it as a guide for what to keep and what to “toss.”

Upgrade your hangers.

We love these flocked hangers, which are available on Amazon. I use them all over my house.

Look at what you have before you buy any organizational tools. 

Before you run to The Container Store, see what you have laying around your house. As you go through the items you plan on keeping; it’s helpful to put them into piles to see how many you have. Have a pile of handbags, belts, sweaters, etc. Then, reuse and repurpose bins, hooks, and baskets to help store them.

Last year, I did end up at The Container Store and found some fantastic items that made a big difference in my space. But I was super specific about precisely what I needed and didn’t waste money on unnecessary gadgets. 

For a list of all my favorite closet organizing items see here. 

A Peek at My Closet



You can see the full “transformation” from the overwhelmed closet after the holidays to the tidy space it is now on my Instagram Stories here. You’ll know that I don’t have a fancy, custom space, but it’s clean, organized, and functional. 

And stay tuned for a formal closet “tour” post next week!

Need to catch up on previous challenges? 

You can view Week One and Week Two here.

Are you following along in our private Facebook Group? If so, post some pictures of your space once you get it organized and share the inspiration!

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

Learn about our mission to help women look and feel their very best, every day, here

Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist





The Well Dressed Life Wardrobe Challenge 2021: Week 3

13 thoughts on “The Well Dressed Life Wardrobe Challenge 2021: Week 3”

  1. Thank you for this wonderful series! I’m struggling with editing. I work in a professional environment, I’m a mom of two young kids and attend church so I really feel like have 3 separate wardrobes. Biggest is work, and then small for weekends and church (I like to wear leggings or fun dresses to church that I don’t normally wear to work). I cleaned out my closet last weekend and got stuck on my 10 pairs of cords! I can’t wear them to work so I do not need 10! Maybe once per weekend I wear jeans or cords. But I’m so fearful of getting rid of them. I feel
    Confident dressing for work but not so much for dressing down on the weekends. Yesterday we went to a fall festival for my kids and I fit right in, but felt like I was looking at what everyone else was wearing. I’m probably trying to hard and worrying too much about what other people think. Maybe I’m just not comfortable dressing casually because I don’t do it often and maybe that’s why I’m feeling anxious! Anyone else feeling like this as they are editing??

    • It’s not unusual for editing to bring up a little anxiety. Specifically when it comes to your cords, for sure, you don’t need 10:). I’m a fan of Emily Ley, she creates fabulous day planners and is an advocate for simplified living. Once a year she does a simplified challenge and has her readers go through their house and declutter. Her motto is to keep only “the best, the necessary and the favorite.” When you find you have too many of one category, use that as a guide and you’ll be able to pair down.

      • So in this case, how many pairs of cords should she keep? I’m having a similar issue with black tee shirts. If it’s something you wear often, how many do you keep?

  2. Hi Meagan, I work full time in a professional environment. Work clothes and shoes are 80%. I have organized my closet. I have 2 but they are not walk in. I know my style. My problem is storage for totes, purses and shoes. I have sliding doors in the closets so I can’t hang anything over it. I have my shoes in clear boxes stacked on the floor of my closet. What suggestions do you have for me to be able to see my clothes, shoes and purses?

    • Hey Sandee,
      I like storing shoes in clear boxes in closets like yours so you can see them, stack them, and keep the dust away. Do you have a shelf in your closet – over the hanging rod. I would clear that, find another place for what you are storing up there and line up your bags. You can use shelf organizers that will help keep the totes and bags stay upright to let you keep them tidy.

  3. For those with no place for over the door hooks. I too have a sliding door. Then Christmas was over and I had command hooks by the bag. I put some in my closed and found shoe holders on hangers, but instead of hanging them on the rod I put them on the Command hooks. Then after the edit I had storage for sun glasses, scarfs, shoes and baseball hats (I like to roll the bill). This was a game changer for my closet space. Hope it helps or sparks an idea for others. Now, what to do with the four Christmas presents from three years ago. Yikes!

    • A lot depends on the kind of space you are dealing with. Personally, I try to hang as much as possible so I can see it right away, also, I have more closet space than I do drawer space. My general break down it: 1 drawer for undergarments, one for pajamas/sweats and one for work out gear. Then I fold sweaters and jeans on the shelves in my closet, swim goes in a basket on a shelf, and everything else in on a hanger.

  4. I’m 87 and mostly retired. I’m 5’1″ and wear petites. I spend a lot of time at home and yet I don’t dress in grungy clothes. I have many pairs of jeans, a few trousers, and a ton of tops. I think it’s time to weed out the tops, but I keep saying to myself “I just got that” when I probably should donate it. I think my problem is that I like to shop. I hope the wardrobe checklist I just downloaded will give me a guide to help me curtail the shopping bug, yet keep what I need and what I will wear. How do I stay away from the clothing shops?

    I do have a little black dress!

  5. Where did you get the clear containers your purses are stored in? Also where did you get the white jewelry boxes and bracelet holders?

    • The jewelry boxes are from Container Store, they are part of their stackable collection. And the bracelet holders I bought on Amazon ages ago. I’ll try to find the links!

  6. My closet shelf space is behind the hanging items, so I have to burrow back to get to the shelves (it’s a rented property, so not permanent). My solution for shoes and purses was to put a cabinet near the front door that can house shoes but can be closed to hide the clutter. I reduced the number of purses to whatever could fit nicely into a few cubby shelves.


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.