Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

The Well Dressed Life Wardrobe Edit Challenge

The Well Dressed Life Wardrobe Challenge has been the cornerstone of our community since I launched it SEVEN years ago!

We would host it three times a year, in the spring, fall, and start of each new year, as a value add for our readers.

But, like everything, it’s time to freshen it up!

The biggest change is that going forward we will only host it ONCE a year, and this year starts on MONDAY, September 18th.

Don’t worry, it’s the same concept, and it’s still totally free. But we’re adding more and focusing specifically on defining your style and editing your wardrobe and closet space.

This FREE, four-week-long event is designed to help you define your style, edit your wardrobe and organize your closet. 

Women of every age, with every budget, in all seasons of life participate.

There is no fee, and it’s a fantastic opportunity to prepare for the new season.

The challenge is based entirely on the system I created when I worked with private styling clients. It’s meant to make the daunting process of tackling your closet a little bit easier.

I break each week down into a series of activities designed to help you:

(1) define your personal style and figure out what YOU need,

(2) edit and organize your closet, and

(3) begin to build a wardrobe you love.

This can be your first or your tenth time participating; it doesn’t matter. Each time you complete the process, you’ll have made a new discovery and gain further clarity around your style.

AND, you’ll force yourself to tidy up your closet 🙂 

But don’t take my word for it, see what some of our participants have said of their experience, taken directly from our Private Facebook Group:

Praise for The Well Dressed Life Wardrobe Challenge:

The Well Dressed Life Wardrobe Challenge

How GREAT Does that Sound?

If you follow the process, by the end of the four weeks, you will:

  • Clearly understand your personal style. 
  • Have a well-organized closet.
  • Feel confident in your choices going forward.

Here’s How it Works:

The new challenge starts on MONDAY, September, 18th.


In the past, we went live with new challenges every Friday, but after listening to your feedback, Monday’s seem like better days for you to get all the information.

You’ll still have a weekend between challenge, but this gives you time to prepare and use your weekend more productively.

In addition, I’ll be LIVE in our Private Facebook Group every Monday of the challenge. Times will be announced shortly.

You do not need to have a Facebook Account to participate, it’s just a nice extra.

Every Monday starting on 9/18 you will have a post from me with two challenges to complete before the following week.

Each week, we focus on a specific goal: 

Week 1 (9/18): We’ll help you figure out your style.

Week 2 (9/25): You’ll prepare for your edit. It’s big job and you need to be ready.

Week 3 (10/2): Now it’s time to get in there and purge

Week 4 (10/9): Finally, we’ll leave you with a break down of the fundamentals of a well-thought-out wardrobe so you always have something to wear.

We move fast on purpose. It keeps you engaged and helps you make decisions quickly.

Here’s What you Need: 

1. A Clothing Rack: I use this under $50 one from Amazon

2. Slim Hangers: You may also consider picking up some new hangers, so you have them on hand when we start to clean up your closet. I recommend these flocked slim hangers. They are my favorite.

3. Be sure Your On Our Email List. If you receive an email from The Well Dressed Life in your inbox every day, you’re all set. If not, fill out this form here

4. Join our community: For even more support, join our private Facebook group and answer the membership questions for fast approval. You can also follow along for extra inspiration on Instagram

And remember, if you’ve already participated, do it again!

You’ll be AMAZED by how much you learn each time. 

A Little About Me (In Case You’re New!)

For the past 20+ years, I’ve helped women get dressed for their real life, first as a retail buyer, then as a personal stylist, and now as the founder of The Well Dressed Life. After graduating from college with a degree in Marketing, I started my retail career as a women’s clothing buyer for large chains and private boutiques. Before starting my first company, I was a buyer for the home-shopping powerhouse QVC.In 2007 I left that position to start Kristel Closets, Inc., an image consulting and private styling firm that operated three offices on the East Coast in Philadelphia, Northern New Jersey, and Washington, D.C. Our company quickly became a leader in the industry, serving busy women who wanted to look and feel their best.While our clients wanted to look modern, classic, and pulled together, they didn’t have the time or energy to do it themselves.That’s where my team and I stepped in.

I’ve helped thousands of women navigate the often overwhelming world of fashion and retail, working with all body types and budgets.

Several years ago, I stepped away from our 1:1 services to focus on building our online business. Today, I provide my expert advice, recommendations, and insights in our daily posts and through these challenges here on The Well Dressed Life.  I use my experience as a former buyer, personal stylist, and busy mom of three to frame all of our content. I like to keep it real, practical, fun, stylish, and kind. It’s About You

I encourage you to use the next four weeks to focus on YOU

Dive right in, ask questions, and get to know your fellow participants, who you’ll quickly discover are the friendliest and most supportive group of women on the internet.

Our challenge aims to give you a clear understanding of what you like and what will work for you so that getting dressed becomes an expression of who you are and not a chore. 

This challenge is for all women with all body types and budgets who appreciate modern, classic style and want a guide to get them there. 

Why is it Free?

I get asked this all the time.

This challenge always has and always will be free.

And the answer is simple. Because I enjoy it! And the challenge has allowed me to understand and connect with our community at a deeper level. And our conversations help fuel our daily content.

All I ask that if you enjoy our site and find the challenge valuable, please share it with your friends! 

So, who is in? 


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.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

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

Kaethe Pittman

Friday 11th of September 2020

Loved it the last time -- can't wait to see what I learn this time!


Friday 11th of September 2020

I'm a first timer! I'm 48 and have no idea what my style is. I'm short and curvy and I struggle with clothes that are to snug or those that make me feel frumpy. I'm looking to find my style. I can't wait to get started.


Friday 11th of September 2020

I’m 57 and this is my first time. I’ll be interested to see what else I can purge. I recently downsized to a condo. Last summer I went through my entire closet and got rid of 10 lawn & leaf bags of stuff! I know I can toss even more!

Heather Bordier

Friday 11th of September 2020

I'm new to this kind of thing. But it definitely needs to happen! Excited to get started!


Friday 11th of September 2020

This will be my first challenge, please sign me up. Thank you for offering it.

Sharon L

Friday 11th of September 2020

This will be my first time. I'm excited about defining my personal style and learning how to buy for it and curate it. I do not have a lot off money to put toward clothes, so I hope I can afford this adventure!

Tracy A

Friday 11th of September 2020

Can't wait! This will be my first time and my closet needs a clean out!


Friday 11th of September 2020

I’m excited to start the Challenge. I used the time during lockdown to sort out my closet and have given so much to charity so I can now see what’s left and I’ve added some pieces and shared them on your fb page over the past few months. I’m sure I’ve only scratched the surface of what’s possible so can’t wait to get started!!

MaryAnn Merrell

Friday 11th of September 2020

I would love to participate! First time! I recently retired so I definitely need a closet makeover.

Kelly A Everhart

Friday 11th of September 2020

I am excited to take the Challenge. I regularly assess my wardrobe fall and spring with mixed results. I look forward to creating a repeatable process!!


Friday 11th of September 2020

This is my first time and looking forward to learning how to dress myself after a 100 lb weight loss. I have gone from size 24 to a 10-12 and still have a hard time seeing myself at that size.

Deanna Debrecht

Friday 11th of September 2020

I'm in! This will be my third time doing the challenge and each time I find items in my closet that no longer fit my personal style and need to go. During the last two challenges, I've become more familiar with my personal keywords - mostly solid colors, chic with fun modern updates, and texture. Over the last few years I've built a solid wardrobe of neutrals, but during the pandemic (and week after week of boredom), I've been finding myself drawn again to my bright winter colors. So this challenge I will be incorporating more color into my fall/winter wardrobe :)


Friday 11th of September 2020

I will be participating for the first time. Looking forward to it!

Kay S Oplinger

Friday 11th of September 2020

This will be my first time, but I love getting your emails every week - such good inspiration! Kay Oplinger


Friday 11th of September 2020

This is the first time I will be joining you in the the fall 2020. I am 76, 5’8” and my weight Is 183lb . I live in Canada, and would like to also know if I can get you picks here. Thanks


Friday 11th of September 2020

This is my first challenge. I'm 58 years old, 5'9", lean limbs but struggle with my stomach area. I live in So Cal and seem to only wear jeans/jean shorts with a t-shirt. I have struggled with clothing/outfits/shopping my entire life. Shopping at retail stores (and thrift stores) is disappointing. Most clothes do not fit me in length. And the quality of what is available in stores is soooo bad. I would like to step up my wardrobe to be more ready for whatever life brings.


Friday 11th of September 2020

This is my first time joining the challenge. I started learning about capsule wardrobes in the spring and want to find classic pieces that look and feel good. I’m in the Facebook group and am excited about the challenge! Thanks for offering it.


Friday 11th of September 2020

I follow your posts religiously. The challenge earlier this year was very timely because the quarantine gave me ample time to dig into my closet and do a thorough cleanup. I’m a very active, 67 year old retiree, and got a great deal of pleasure giving away suits and heels and concentrating on my current lifestyle. Love that you do the legwork for clothing and misc. items and I’ve never been sorry following your advice. (PS: I have two daughters very close to your age and they come and shop MY closet. 😌) Thanks for what you do!


Saturday 14th of March 2020

Hi Megan I love your site ❤️I am retired 65 years old I live in the uk . My style is classic ( Kate Middleton ) . I am sure you must have covered this before but could you help me with this problem I like to keep a special occasions wardrobe for things such as lunch with friends and coffee with friends smart/ casual nights at restaurants with friends I keep this separate because my other stuff I replace frequently and my occasion wardrobe I tend to pay more money for but I have far too much in it!! Could you please help me with outfit ideas and how many outfits I need for this wardrobe thank you regards Jackie

Betty Quinn

Friday 6th of March 2020

This will be my first time doing the challenge. I've tried to do a capsule wardrobe before, but quickly get sidetracked or lose interest. I'm looking forward to the Friday focus reminders.

Ginny Tugwell

Friday 6th of March 2020

Hi this will be my first challenge..looking forward to it..I am starting a new job next week and that is one reason for joining now...however I am on the FB group and missed the previous challenge. I love expressing my personality through the clothes I wear and look forward to exploring this further with you all.

Alice Caltrider

Tuesday 3rd of March 2020

I've been following "The Well Dressed Life" for awhile now but have never participated in the challenge before. Looking forward to it. I am newly retired and trying to adapt my wardrobes (one up north and one in Florida) to this change in my lifestyle.


Tuesday 3rd of March 2020

Looking forward to the challenge! Just joined this group so this is all very new to me


Monday 2nd of March 2020

I am participating for the first time! Looking forward to the experience.

Kristen K

Monday 2nd of March 2020

I am looking forward to participating in the challenge for the first time. The timing is perfect because March is when I start thinking about my Spring wardrobe. I promised myself I would spend wisely this year and curate a closet with fewer and considered pieces. I am in my 50’s and petite. I am finding it harder every year to find pieces that fit my desired style: classic and well made, with a healthy mix of current and edgy pieces.

1 2 3 4 5