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The 2023 Wardrobe Challenge: Week 2

Welcome to week two of our Wardrobe Challenge!

There have already been some big takeaways after week one, and they are exactly what I was hoping they would be!

If you are just joining us, or are running behind, don’t worry. You can start at Week 1 here.

Go at your own pace and utilize our FB group to keep you motivated and on track. 

Be sure you finish each challenge before moving to the next. 

Week 2: Edit Your Style and Closet

Challenge #1: Edit Your Pinterest Board

This part of the challenge always creates the most conversation. 

You might think you need to pick a style and commit to it. 

We’re often told we are either “classic,” “trendy,” “boho,” or whatever. Like we have to choose a lane and stay there. 

But the truth is we are all a unique combination of many things. 

For example, I used to think I was “preppy.” 

But I’m not.

I like elements of preppy style.

I never pass up an opportunity to monogram something, and a good chunk of my wardrobe is from J.Crew.

But I’m not fond of bright colors and prints; I prefer saturated neutrals, stripes (obviously) and better fabrics. 

After going through this process for several years now, it’s clear that my style is classic and modern with a twist. 

That “twist” is usually an interesting detail, a splurge-worthy piece, or an unexpected personalized element – like a monogrammed bag or bold accessory.

To help you with this, go through your Pinterest Board and only keep the images you LOVE. 

You must LOVE every pin. (I know! It’s hard.)

The Difference Between “Liking” and “Loving”

It’s not just what you like, it’s what you want to LIVE in.

You can appreciate all the different styles. 

But narrowing down to the ones you want to wear all the time and starting to understand how you can adjust your style to your life is the point. 

Take a few minutes to write down what you dislike, like, and love.

Mine are below:

I also love crisp white shirts, and slim silhouettes (note, I’m curvy and still wear slim shapes – more on that later)

I could go on and on, but this just an example.

Remember, this is personal.

I dislike ruffles ON ME. They look lovely on others.

Doing this exercise forces you to think about your preferences and ensures your wardrobe mixes and matches well, and that you always look and feel yourself. 

Find Your Common Theme

Next, review your edited board and look for commonalities and consistencies.

It might not be abundantly clear, but stick with the challenge; it will start to show itself.

You can keep pictures of outfits you think are not suitable for your body type. Your board is pure inspiration.

Any style can work for any body type with proper adjustments to make you feel comfortable.

What we’re looking for here is a theme.

Some a-ha’s you might have:

  • You pinned lots of jeans and pants but have a ton of skirts collecting dust in your closet.
  • Maybe you pinned a dozen monochromatic looks yet own lots of patterned tops and dresses.
  • Do the outfits on your board have scarves and accessories, but you never incorporate them into your daily outfits.

If these are the revelations you have as you finish up this part of the challenge, you are right on track!

Challenge #2: QUICKLY Edit Your Closet

You can do this next step all at once or over a few days; it depends on how much you have in your closet.

Set up a workspace in or close to your closet. Designate four piles:

  1. Keep:  For anything you know you love, use regularly, and fit in your style.
  2. Mend:  Keepers that need to be tailored, cleaned or repaired.
  3. No’s: Items that do not help you achieve your desired style. 
  4. Maybe: Use this as a parking lot for items your undecided items.

Having a rolling rack for this exercise makes it easier to stay organized.

I use mine for the “keeper” pile.

Next, take your Pinterest board  into your closet.

Quickly Edit Your Wardrobe

With your inspiration pictures as your guide, QUICKLY, go through your wardrobe. 

Hold every piece up and ask yourself, does this get me to where I want to be?

If your answer is “yes,” put the item in your keeper pile or rolling rack.

If your answer is “no,” put it in your no pile.

If you have no idea or don’t want to deal with it, put it in the maybe pile.

We’ll deal with those items next week.

Do this quickly. The maybe pile is there to take away any pressure.

You will likely have to keep a few pieces that are just okay so you can get dressed in the morning. 

Put these in the undecided pile too. The most important part of this exercise is to see if or how much of what you are buying reflects your style.

Once finished, go through the no’s and decide how you want to process them.

You can donate, resell, recycle, or they go right in the trash.

Hang and fold everything else.

Put your undecided pieces back in your closet, behind the pieces you love, so your favorite items are the first thing you see.

Please don’t focus on organizing anything yet (you can guess where we’re going next week).

Repeat the same editing process with your shoes and accessories.

While you’re in your closet, ask yourself these questions and write down the answer:

Is your current wardrobe reflective of the style you love?

If not, what is your motivation for making purchases? (Sale price, impulse, need, etc.) 

What do you have more of, basics or trends?  

For example, my Pinterest board has always been primarily neutrals and solid colors, yet I had at least a dozen print blouses and tops hanging in my closet when I first created this exercise. 

There was nothing wrong with them, except I don’t like many patterns, and I wasn’t wearing them.

So why do I keep buying them?

In my case, I equated pattern with variety.

I was also using Stitch Fix at the time (I had just had a baby) and kept many pieces they sent only because they were okay-enough and fit.

Once I completed the exercise, I permitted myself to let go of what didn’t fit into my style.

You may not have many things in your current wardrobe that reflect your style. If you do, you’re way ahead of most of us!

It’s okay to feel frustrated. Take a deep breath and trust the process.

These steps will allow you to discover what you like, understand your decision-making process when shopping, and eventually help you fill your closet with items you can’t wait to wear.

The process of creating a cohesive wardrobe is not immediate and it always ebbs and flows.

That’s why so many readers do this challenge every season.

It takes time to curate your look, find the pieces that work best for you and, of course, work those purchases into your budget.

But after this challenge, you’ll be off to a great start.

If you’re just joining the challenge, start with Week One, follow the link below

The Well Dressed Life Wardrobe Challenge: Week 1

Join Our LIVE Q&A

Join me on Tuesday, September 26th at 3pm EST for our Week 2 LIVE over in our Facebook Private Group.

Note, this week’s LIVE is on Tuesday not Monday to respect Yom Kippur.

I’ll recap Week 1, set you up for Week 2 and answer any of your questions.

The 2023 Wardrobe Challenge: Week 2

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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Friday 15th of September 2023

i love these challenges1 been with you for four years now. It will be difficult to only do the challenge only once a year! Thank you for the challenge!!


Monday 16th of January 2023

I am having trouble finding the links to the FB chats here. I am hoping I can access those without having an FB account. If you can point me to where I should look, I would appreciate it.


Friday 9th of September 2022

I love your wardrobe challenge!! Whenever it rolls around I participate!!! I keep learning more about my style!! My closet never looked better!! I'm in my mid-fifties and find this is a great idea even for mid-life and I'm doing it then beyond!!! Thank you so much!!!!

Mary Ziebell

Monday 13th of September 2021

Greetings! Of all the fashion bloggers I follow, I truly love this one the most. I'm enjoying this process of defining my style and purging the closet. My issue is that I have registered several times for the free Wardrobe Checklist and have not gotten anything sent to my email. Before you ask, I've already looked in the Junk and Spam folders. What am I doing wrong? I really thing this would be a useful piece of information! Thanks all!

Elle Waters

Tuesday 9th of March 2021

This is so helpful. I am going through all the parts and am loving it, Thank you for sharing!

PatC Fields

Thursday 18th of February 2021

I put together a board and think I know how I will be putting outfits together. It has already helped. As for lifestyle, there are 2 items. I am staying at home or traveling/going.


Friday 25th of September 2020

I bought a cloths rack and plan of going through my closet tomorrow. Will today’s Face Book live class be posted to Facebook. I couldn’t figure out how to join in. Love the group!


Thursday 23rd of January 2020

My aha! Was when I realized I had blouses from years past that I haven’t worn for ages. I kept them to wear with a pant style that has long since disappeared. I was keeping them just in case. Of what I don’t know, but there they were covering up items I wanted to wear and couldn’t find. I also found several short cap sleeve tees. They don’t not look well on me. Time to pass them on.

Megan Kristel

Saturday 25th of January 2020

Such a great take away! Thank you for sharing!!!

Dawn Price

Saturday 28th of September 2019

Hi Fellow Wardrobe Challengers! This was very interesting for me! My board was completely full of neutrals, a couple of dusty pastels, virtually no prints except for a handful of leopard, oversize plaid, stripe and blocking - all neutral. Meanwhile my closet is full of prints and colors! LOL!!! No wonder I can never find anything I want to wear! ;) (BTW I've Kondo'ed my closet a few times.) I think the problem is that I LOVE color just not to wear it. My house is full of color. So weird. Anyway, that's my Aha.


Friday 8th of March 2019

I am really into the idea of figuring out my style, and so far I have done all challenges of week 1 and the first of week 2. However I seem to be a little stuck.... This is a link to my pinterst board: I pinned everything I liked and now narrowed it down to things I really like; but since in challenge 1 of week 1 we didn´t have to pay attention to body type or lifestyle/ budget I pinned a lot of things that will be too over the top for everyday life (I work part-time in an office; I occasionally go out or meet with friends, and I spend a lot of time in my own home) additionally I am not sure whats my "common thread"....

any suggestions? I would really appreciate the help

Megan Kristel

Wednesday 13th of March 2019

Hi Lillien - are you part of our Facebook private group? Please join there so you can benefit from a more robust conversation about the challenge.

Denise Richards

Tuesday 2nd of October 2018

Hi loving this blog. I turned 60 in June and desided to spend more time on my appearance so I did the first challenge in July. I finished the second challenge last month. These challenges make it more fun can’t wait for the next one. Thanks


Thursday 21st of October 2021

@Denise Richards,