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The Well Dressed Life Wardrobe Challenge 2023: Week 4

Welcome to week four of our Wardrobe Challenge!

Today we wrap up our last set of challenges for our Wardrobe Edit Challenge.

But before we jump in, I have to thank everyone for participating with such enthusiasm!

This week is going to wrap up the challenge, but not the process. 

Remember, it takes time to put all this into practice.

Once you figure out what you need, it’s time to do the work to not only find those items but figure out how to translate all those gorgeous inspiration pictures into an outfit that will work with your lifestyle, budget, and body type.

If you are new to our community, I encourage you to ask specific questions and request posts covering different topics.

Our readers influence every piece of the content we share. I base my daily recommendations and tips on our conversations.

Use our archives while searching for inspiration. Every style post is filled with inspiration and guidance and offers recommendations for all sizes. 

Simply type what you’re looking for into the SEARCH box on the ride side bar of our homepage.

Week 4: Create New Outfits and Write Your Wish List

If you haven’t completed week 3, please do that first.

Do not stress out if you are just starting, or feel like you’re running behind. This is suppose to be fun and support is available in our Facebook group no matter where you are in the process. 

If you are having a hard time letting go of some of your items, read this post about the mindset shifts we need to make in order to gain control of our closets. 

Challenge #1: Create New Outfits

Spend some time in your clean and organized closet.

Doesn’t it feel so good?

With the clutter removed you might be amazed at the outfit combinations you never noticed.

Every time I go through this process I always find a new way to wear something, discover an old favorite, or simply get re-inspired. 

And there is just something so motivating about a clean, tidy closet. 

So now it’s time to build some outfits. 

To guide you, use your curated Pinterest boards and your lifestyle diagram. 

The idea is not to replicate each look.

Instead, be inspired by them. Look at the color combinations, pattern pairings, layers, and accessories. Those are the essential elements. 

Use your Lifestyle Diagram as a guide and try to create 1 -3 looks in each category. 

Mix and match pieces, repeat a basic, see how far you can take it. 

You may be please with what you can make with less, OR you may need to begin rebuilding your wardrobe. 

Here’s an example of how I recreate a look: 

I pinned this image of Victoria Beckham because I love how it mixes casual and elegant elements.

To be clear, there is no one on earth LESS like Victoria Beckham than me.

We have very different body types, she’s petite, I’m a foot taller, probably a hundred pounds heavier, and our lifestyles and budgets aren’t even in the same stratosphere.

It’s not the same outfit.

Instead, it’s inspired by the pin, which is likely made up of pieces from her collection and other brands I can’t afford.

Instead, I pulled out my favorite dark skinny jeans, an inexpensive white blouse, a camel coat I found at H&M a few years ago, and heels.

If you don’t want to wear heels, wear neutral pointed flats instead.

I would put this in my Social category; I’d wear this to lunch or a casual meeting.

Then I would swap out the blouse for a white tee and add a pair of sneakers and put in my Mom-ing category.

So you can see how elements of one outfit will carry through multiple categories.

Do not try to recreate looks, be inspired by the feel. See here for another example.

Challenge #2: Write Your Shopping List 

As you work through your wardrobe, creating new looks, you’ll start to notice what is missing. 

Jot down what you need to create more outfits.

  • Could you use a different style pant?
  • Maybe an updated shoe would pull several looks together.
  • You might need something as simple as a cami so you can start to wear a lightweight sweater.

Write down anything that would add more life to your existing wardrobe.

Keep this list with you (I keep mine on my phone) and only purchase from the list!

By doing so you will stay focused, and your wardrobe will become more functional.

If you buy things that are not on the list, you’ll end up with a closet full of items you don’t need all over again.

Bonus Challenge #3: Your Three Words

Now that you have some clarity, how would you describe your style? 

Come up with three words and keep them with you as you make decisions going forward.

In full disclosure my words have changed over the years, because our preferences change and new styles are introduced. So you are not married to these words, rather, consider them an every-changing guidepost.

Mine are: Timeless | Casual | Feminine

Timeless my core wardrobe pieces are fresh versions of classics.
Casual: because my lifestyle which is far from formal.
Feminine: I like pretty things, soft make up, “girlie” accessories.

Bonus Challenge #4: Where Do You Make Your Mistakes?

Now that you are wrapping up the challenge, take a minute to think about where you are making your shopping mistakes. 

I realized only recently that I have two BIG areas of improvement. 

The first is when I panic shop before a vacation. I end up not liking/needing/using 80% of what I buy.

So I know I have to be more organized before a trip. I need more time to pull outfits together and not wait until 48 hours before a flight.

The second is discount stores. I need to stay away from them. I buy the dumbest stuff because I fall into “oh, it’s on sale” and get all impressed with myself, like, look, I can save money!

But my truth is, for what I spend on a visit to TJ Max or Off Fifth, I could have bought one or two investment pieces that would better serve me.

Think about your areas of improvement; they’ll be different than mine. And consider solutions to avoid them in the future.

Enjoy your new space and the fresh start!

Your closet won’t always look this great.

Life will get busy, and you’ll need to regroup. The good news is it will be so much easier to keep it tidy now that you have a system.

I follow this process twice a year, only it doesn’t take four weeks; it takes about an hour to get back on track.

Remember that your wardrobe is ever evolving.

You’ll never be “done.”

There will always be something on your shopping list, an item that needs to be replaced or a new look you want to try.

I hope that after this exercise, you start to hold your purchases to a higher standard and realize you don’t need so much, you just need the right options for you.

Join me in our Private Facebook Group for a LIVE Q&A!

This week we’re doing our last Facebook Private LIVE Chat today, October 9th at 3PM EST.

The Well Dressed Life Wardrobe Challenge 2023: Week 4

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Ruth K.

Monday 9th of October 2023

I didn't do the wardrobe challenge this time around. However, I have in the past. But wow, Megan! The Bonus Challenge #4 was an epiphany! I also need to stay away from discount stores. I have SO many bargain tops that need to be edited out of my closet! I also realized that my past participation has helped me know what my wardrobe needs, and it's easier to get rid of things AFTER I have filled some of the holes in my wardrobe. I guess I'm doing it kind of backwards, but it works for me. The Wardrobe Challenge has been THE most helpful thing for clarifying my style, cleaning out my closet, and developing a functional wardrobe. Thank you, thank you, THANK YOU!

Carolyn in Texas

Monday 2nd of October 2023

Dear Megan - Though we have never met - thank you for being a friend. You provide honest, experienced, loving, instruction on how I, and all of your followers, may improve an area of my life that is important and challenging.

I’ve bumbled about for years and for the first time I’m approaching a closet that contains a wardrobe of personal style (MY personal style) that I’m pleased with. Thank you.

Kim Carter

Friday 27th of January 2023

Looking forward to capsule wardrobe planning. Need to create one for warm weather and one for moderate to cold weather. Also need advice about wearing nylons and tights...yes, no or personal choice? My legs are very pale with spider veins.

Karen Coxe

Friday 27th of January 2023

Hi, Megan. Still working on week 2. My concern is being short and plus size, so many stores don’t carry much, if any, inventory anymore. I wind up doing a lot of shopping online. Of course I have to return a lot of things. Is there a strategy for online purchases that idk so I don’t wind up returning so many items that don’t fit or proportions are wrong? The Challenge has been helpful! Thank you!

Silvia Benincaso

Friday 27th of January 2023

The Wardrobe Challenge combined with your recent Outfits in Real Life posts have finally made me "get it." I am guilty of the emergency shops before every trip and have finally started planning my purchases, when needed, with intention. Thank you.


Friday 23rd of September 2022

Not finished with my closet cleanse but I will finish and move on the week 4!! I've been doing this for several years now and love the results!!!

Megan Kristel

Tuesday 27th of September 2022

Awesome and love hearing this. Keep going!

Jeannie J

Sunday 24th of April 2022

I did not receive my Sundays Sales email. I went to Facebook and saw it posted there. Is this the new process?

Megan Kristel

Sunday 24th of April 2022

You did not receive the email because you unsubscribed from our email list on April 22nd.


Friday 28th of January 2022

I love how you've made this so easy to follow and accomplish within 4 weeks! I've started muy list and am looking forward to move back into my home after renovation. That means my closet will be already done! Thank you too for giving me a boost into really looking at my true style since I'm retired. I'll be ready for anything by this spring/summer. Keep posting and again thank you so much. B

Kaethe Pittman

Sunday 26th of September 2021

I, too, would really welcome a capsule wardrobe guide/column/tip sheet. And I love the outfit you "copied" from Victoria Beckham -- your version is nicer and much classier!


Saturday 25th of September 2021

What’s going on with the front of the dress?

Mary Ann

Friday 24th of September 2021

Love this site. Any suggestions for a festive evening, October wedding in New Orleans?(pear shape) And could you remind me of your self tanner please?


Sunday 31st of January 2021

Every thing you read, it says your colours change once you let your hair go gray? Could you do a article on this. Do you go deep, lighter in your colours. Enjoy reading your daily newsletter. Thank you


Thursday 15th of October 2020

I’m still waiting to get added or approved to the private FB group.

Megan Kristel

Thursday 15th of October 2020

Everyone who answered all of the membership questions have been approved. All questions need to be answered so I can make sure we do not allow spam accounts into the group.


Friday 9th of October 2020

My closet looks so great and now it is easy to find everything. I even got organizers for my bras and underwear...amazing how good it feels! Thank you for being so helpful and encouraging!

Deanna Debrecht

Friday 9th of October 2020

Here's another tip for searching Pinterest - by adding an extra descriptor, you can narrow the search results; so you can search "black jeans outfits over 40" or "black jeans outfits plus size" or "black jeans outfits curvy" or something like that to try and get more specific results.


Saturday 4th of April 2020

Love the idea a searching for “one piece” on Pinterest for outfit ideas. I don’t need anything new, I just need to figure out what to do with what I already have in my closet!

Moon beams

Thursday 6th of February 2020

THANK YOU for leading us through this exercise! I had let myself fall into a sad routine of wearing the same things every week instead of actually making outfits with my capsule and accessories. After taking a look at my wardrobe, I realize that I am actually in good shape. I need a new pair of white sneakers and I really want to add a pair of red side-zip pants to the mix or perhaps red jeans might work better since mostly I wear casual outfits that I can take to more polished with accessories. The pants would work with both my winter base of black and my summer base of navy.

Alison Sinclair

Monday 3rd of February 2020

This has been great. The big eye opening moment was when I realised that my wardrobe didn’t look anything like my Pinterest boards. The result of shopping without a plan, looking to brighten my self up and the dreaded “it will do” purchases. Time for the heavily patterned tops to go and in comes the more classic neutrals as per my board. Thank you for giving me a plan.


Sunday 2nd of February 2020

I loved this assignment!! I was feeling in a rut with my outfits, but after perusing my Pinterest boards, I quickly came up with 7 or 8 new outfits from pieces I already have! I can already tell just from those 7 or 8 outfits that they will inspire even more! <3

Megan Kristel

Sunday 2nd of February 2020

That's so awesome!!!


Friday 31st of January 2020

I can't wait for the capsule wardrobe list! Super easy. One for casual mommy-ing and one for professional work days would be amazing!

This process has been one worth doing. I feel like now that I am in my late 30's and have two small children I need to get rid of that dress I went dancing in when I was 21 and heels I can't even walk in anymore and trade up for a pair of spanx leather leggings and cute top. I really appreaite your insight on how to pair items together and the links to purchase. Very helpful for the women who hates (and I mean HATES) to shop.



Friday 9th of October 2020

I can relate! I'm 37 and have an eight month old. I got the Spanx "leather" leggings about six months ago and I love them! Hot top, they run small. I'm usually a size 8-10 and I wear a XL. They are great under a short casual dress or a long sweater. Another hot top, thrift stores are bursting with great clothes right now. Everyone is getting rid of good stuff. I go in looking for baby clothes and usually come out with a few pieces for myself as well.

Dawn Price

Friday 25th of October 2019

What happened to the "Facebook LIVE Q&A on Wednesday, October 23rd from 7:30 – 8:30 EST"? I looked all over the place for it at the time. I've never participated in such an event but couldn't figure out where it was. Did it happen? I was really disappointed to miss it. If you could next time leave instructions with the date/time on how to get to it that would be very appreciated.


Wednesday 16th of October 2019

I would love a capsule wardrobe list to stick to....keep it simple stupid for me :) I get tired of wearing jeans/tennis shoes (needed for arch support and to fit my custom orthotics) and would like some other casual pant options that make an aging, ie pancake backside flattering. I think limiting myself to the capsule would feel liberating and I would not always be looking at something unnecessary, outside of the 'sule' :) I do have a closet full of things I don't wear or don't know how to pair.

Kathy Rubin

Monday 4th of February 2019

Love it!


Wednesday 17th of October 2018

I love clothes! My closet is splitting at the seams, I’d guess you’d say I’m shopaholic! What I’m going to do with all of the pieces that I need to get rid of? I’ve taken a lot to consignment a store, I need to stop buying! HELP!!!

Megan Kristel

Wednesday 31st of October 2018

Have you looked into Thred Up and Poshmark? We have a recent article about selling and donating best practices here.

Virginia Todd

Tuesday 16th of October 2018

This process has been wonderful for me to determine who I am with regard to image. Thanks for sharing your talent and insight.

Megan Kristel

Wednesday 31st of October 2018

Thanks Virginia!