The Well Dressed Life Wardrobe Challenge 2020: Week 4

4 Weeks to a Better Wardrobe - Part 4 - The Well Dressed Life
Four Weeks to a Better Wardrobe - Week 4 - The Well Dressed Life

Happy Friday, Ladies!

Today we wrap up our last set of challenges. We’ll focus on discovering new outfit combinations you already own, making sure you have what you need for all aspects of your busy life, and creating a strategy for going forward.

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

It has been so fun to see everyone’s closet “after” pictures. This round especially showed us so many examples of how to get creative with organizing a closet. It’s beneficial to see regular closets instead of the unrealistic ones we see on Instagram and Pinterest.

One of the things that set this site apart from others is that our readership genuinely fuels it. I never wanted to start a blog to talk about myself (you would be so bored). So while I certainly feel a connection with our audience, even friendship in many cases, I want this to be a resource first and foremost. The content produced here is inspired explicitly by your comments, questions, and requests.

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

Remember, it takes time to put all this into practice. That’s why so many women do this challenge every season. 

Now that you know what you need, it’s time to do the work not only to 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 post on this site. I consider our readers more like clients, so the recommendations, tips, and advice I share are all deeply considered based on everything I know about you.

Use our archives while searching for inspiration. Almost every style post notes how to translate each look based on size and body type.

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I guarantee the more you participate in our community, the more you’ll get out of it.

And I’ll be here to help! 

Starting with a LIVE Q&A in our Facebook Group – Details Below! 


Week 4: Create New Outfits and Write Your Wish List

If you haven’t completed week 3, please do that first. If you are just starting, or feel like you’re running behind, do not stress. This is suppose to be fun!

Take your time! There is no rush. These posts will remain on the site for you to reference. If you use Pinterest, you can pin these to a board for easy access.

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 or rediscover an old favorite.

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

My closet – after the edit.

To guide you, use your curated Pinterest boards and your lifestyle diagram. Try to recreate a few of the looks for each of your categories. 

Use Pinterest as a search engine. Say you have a pair of black jeans. Type “black jean outfits” into Pinterest and be amazed at how many ideas you get.

Yes, I know the pictures on Pinterest are almost entirely of young, super-thin, super-tall women in four-inch heels

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. 

You may want to swap out a skinny jean for a straight leg or wear a different shoe. We all have to make adjustments to meet our specific needs. 

Here’s an outfit I “found” after I did this challenge in January right before the world shut down.  



View this post on Instagram


🎉How many unknown outfits are hanging in your closet?? . 🥂For date night I gave myself 2 challenges: . 1. Find an outfit I didn’t know I had, . 2. No jeans! . 🤚🏼So many of us go to jeans all the time. . I know I do because my life is super casual and jeans just fit me better. . I’m THRILLED with this outfit. . I had both pieces in my closet and never thought to put them together – and this is what I do for a living! . It shows how important it is to have an organized closet (you have to see your stuff!) and you have to give yourself a minute to look through what you have. . I love a monochromatic moment that combines various textures like the knobbiness of the sweater and the shine of the silk skirt💕 . And, this outfit was so affordable. The sweater was under $30 and the skirt was on clearance for $20. . So carve out some time and see if you can find the hidden looks in your wardrobe! . Swipe to see tagged retailers in picture. . 👼Photo-bomber just turned 14 months and is fresh out of the bath💕

A post shared by The Well Dressed Life (@thewelldressedlife) on

Remember to use your entire wardrobe. Break up “sets,” and incorporate pieces you are saving for a schedule special occasion.

Pro Tip! Take pictures of your outfit options and keep them on your phone so they are at your fingertips when you need a reminder.

Challenge #2: Write Your Shopping List 

As you work through your wardrobe, creating new looks, jot down what you need to create more outfits.

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Could you use a different style pant?

Maybe an updated shoe would pull several outfits 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.

AND share your shopping list in our FB Group. I use all of the conversations on that feed to help create posts for each season.

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!

On Sunday, October 18th at 7pm EST, I’ll host a Facebook LIVE, answering all of your questions, sharing tips, and my best advice to keep your closet organized, and begin to build a wardrobe you truly love. 

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To Join our Facebook Private group simple follow this link. Be sure to answer all three membership questions. 





18 thoughts on “The Well Dressed Life Wardrobe Challenge 2020: Week 4”

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

  2. 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!!!

  3. 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.

  4. 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.

  5. 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.


    • 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.

  6. 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

  7. 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.

  8. 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.

  9. 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!

  10. 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.

  11. 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!

    • 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.


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