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

Our last challenge focuses 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.

Week 4: Create Some Outfits and Write Your Wish List

If you haven’t completed week 3, please do that before you get to this one. And 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.


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. You don’t need to completely copy it, just be inspired by some of the looks you pinned.

A good tip to consider is to use Pinterest as a search engine. Say you have a pair of black jeans.  Simply type “black jean outfits” into Pinterest and be amazed at how many ideas you get.

Here’s an outfit I “found” after I did this challenge in January: 



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🎉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💕

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Remember to use your entire wardrobe. Break up “sets,” and incorporate pieces you are saving for a yet to be 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 for 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 what you need in the comments below so I can help you find it! 

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 TODAY!

We’ll recap last week, set you up for this week, answer any of your questions, and let you know what to expect in the coming weeks. To join just follow this link, and be sure to answer the three membership questions. 

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13 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.


  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!


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