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The 2023 Wardrobe Challenge: Week 1

Ladies, today is the day we start to get your style and wardrobe in order!

Whether you work in or out of the home, have little kids at your ankles or grown adult children, are getting back in the workforce, are blissfully retired and focusing on your passions, or are simply ready to reconnect with yourself, this challenge is for you.

Our four-week series is for real-life women of all shapes, sizes, lifestyles, and budgets.

If you love classic style and want to make getting dressed a whole lot easier, this is for you. 

Here’s How the Wardrobe Challenge Works:

Every Monday for the next four weeks, we share two challenges.

Taking your time with each challenge is essential, but just be sure to finish each challenge in order before moving to the next.

I designed the Wardrobe Challenge to build upon the previous week’s tasks. 

You can follow along with the group (join our Private Facebook group to interact one-on-one) or go at your own pace. 

I’ll be on a LIVE In our group today at 3 PM EST to review this week’s challenges. 

Week 1: Finding Inspiration and Your Personal Style


Challenge #1: Discover Your Style

In 2007 I started my personal styling and shopping business, Kristel Closets.

The first appointment with a client would be in their closet, where we we talked about her clothing challenges, likes, and dislikes and did a quick edit.

During those first few hours, I noticed that almost every client had trouble describing their style. 

It didn’t take long for me to realize that we needed a visual to articulate each client’s unique personal style.

So I created a series of pre-work for them to complete before our first appointment, designed to help the process move smoothly and efficiently.

I was always aware of our private clients’ investment when they chose to work with us, so this was a way to ensure we got on the same page as quickly as possible and spoke the same language.

Pull Inspiration Pictures

A big part of this pre-work was pulling inspiration pictures. 

Clients who took the time to complete this tasks had the most success, and the same goes for participants of the challenge.

Do not skip this part. 

Many of you are looking to streamline and simplify your wardrobe; others mentioned that they recognize style in others but have difficulty translating it for themselves. 

And an overwhelming majority of participants say they simply have too much in their closets.

Without a clear understanding of your style, you will not be able to edit down your wardrobe.

This first challenge allows us to create a filter for future decision making. These inspiration pictures will help you purge your closet and shop better.

And you will begin to recognize what you like quickly. 

We recommend Pinterest to help organize these images, especially for this challenge. It’s a great place to search for and share ideas. 

Above is a snapshot of my personal board.

Pinterest Image Exercise

1. Log into/ Set Up an Account on Pinterest.

2. Create a Board called The Well Dressed Life Wardrobe Challenge. 

3. Begin to search for images. When searching, type in words like classic style 2023, workwear 2023, casual outfits 2023*. 

4. “Pin” those images onto your board, at least 20. 

*Adding the year to your search word is super important, so the most current images show up in your feed. 

For now, do not think about your body type, budget, or whether it’s appropriate for your life. Pin anything you like. 

Challenge #2: Define Your Lifestyle

Our lives are continually evolving, but our wardrobes tend to stay the same.

If you have changed jobs, got married or divorced, had a baby, had another baby, left the workforce, retired, or you’re reseting after the past few insane years, this exercise will help you get clear on your needs.

To get a visual of how and where you spend your time, create a Lifestyle Diagram.

It’s easy; draw a circle on a piece of paper to create a pie chart. Now, break down your life according to percentages totaling 100%.

Include work, activities, travel, date nights, anything you spend time doing. It’s essential to see how you are spending your time and what is coming up on your calendar.

You might find you’re buying a lot for work but have nothing to wear on the weekends. 

When I first did this exercise, I didn’t have enough options for social outings and date nights. Today, I need more sporty, casual pieces for weekends on a sideline somewhere.

Tip! We have had some participants take this very seriously! They went so far as to create an Excel spreadsheet and pie chart to capture their percentages.

Here’s My Lifestyle Diagram:

You can organize this in whatever way makes the most sense for you.

For example, we’ll have a few trips to Florida this fall and winter, so I’ll need some warmer weather pieces on hand, but then in the spring, with a million tournaments and regattas on weekends, I’ll need more athleisure.

Complete both of these challenges before you start the next round of challenges in Week #2.

And please note, for this Challenge, our Weekly Facebook LIVES will be on Monday’s at 3pm EDT, in our Private Facebook Group. If you can’t join us live, the video will be posts in the group and at the bottom of this post once the session ends. I’ll go over each week’s challenges, share some tips and answer all of your questions.

The 2023 Wardrobe Challenge: Week 1

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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Saturday 30th of September 2023

I miss not seeing the wardrobe Pinterest boards in our Facebook. So much of Pinterest is ads. Looking at the boards of others I was able to find more complete outfits. Thank you for all you do.

Megan Kristel

Sunday 1st of October 2023

The volume of boards people were sharing became annoying to members not in the challenge, and I was inundated with messages demanding to know when their boards would be posted. It just became too much to manage, but, you can still see pin boards in the facebook group from previous challenges.


Saturday 23rd of September 2023

A beginner-lost husband in February. Have begun my new life at 75 yrs and need some help transitioning from sloppy lake-time person to person surrounded by upper class ladies in a 55+ senior residence setting.


Tuesday 19th of September 2023

How do I view the video for week 1 challenge. I do not have a Facebook account, therefore, I cannot get into the private group. Thank you


Friday 6th of January 2023

Trying to figure out the percentages of time I spend on various activities because often I run errands or stay dressed in my workout or golf clothes for most of the day after I finish these activities. So how do you account for that? Are the percentages based on time spent in each activity per week?


Sunday 25th of September 2022

Do you know of an on-line app that I could take pictures of all items in my closet that would automatically make outfits for me? I struggle with putting outfits together and seem to always wear the same thing. I have recently retired from a very conservative line of work where I wore suits and need help with day to day semi conservative age appropriate outfits. I know my closet is full, I just can't put outfits together without help. Thank you.

Megan Kristel

Tuesday 27th of September 2022

I don't personally use it but many readers like the Stylebook Ap. :)


Friday 2nd of September 2022

I'm excited to try this out! I'm just struggling with my age (mid 50s) and my tastes (mid 20s) plus much more work from home and much less office. I still prefer my office clothes so need to find my wfh style. Almost makes me want to re-join facebook, but not quite. :-)


Saturday 2nd of April 2022

I’m so glad I decided to try the Wardrobe Challenge! At 62, you would think I would have some idea of what types of clothes I should be wearing to make me look my best, but, nope. I have had a Style board on my Pinterest account for years, and the things that I have pinned are still the looks I gravitate to, but in my real life (I am retired, care for my granddaughter part of the week, do some light yard work) my main goal when getting dressed is usually to be as comfortable as possible. On Pinterest I did the searches you suggested, and right away I saw quite a few things from my closet that I can consign or donate. I am excited to continue on and see what happens! Thank you for making this available.


Friday 1st of April 2022

Hi! I’m excited to try your challenge:-) I’m a teacher and a hockey mom 3/4 of the year so need ideas for staying warm without bulking up. For teaching; I do like combining jeans with somewhat nicer tops and comfy shoes are a must! I occasionally wear dresses or skirts, and will change after work, but other wise like outfits that can go from the classroom to the carpool and wear a lot of the same things on the weekend. This all probably makes up 80% of what I spend my time doing. As my kids are getting older, and CoVid is ending, I’m starting to spend time going out to lunch, to museums or to dinner. I also like to be able to go for a walk or even a bike ride without having to change. I’m happy with my yoga clothes and PJs, already. I noticed on some pie charts, people named a style for different parts of their time…I definitely don’t have the vocabulary to quickly describe what I like. Maybe casual with a little trendy or dressy edge thrown in?

Christina Mills

Friday 1st of April 2022

I hope I am registered for Aprils challenge. Excited.

Megan Kristel

Friday 1st of April 2022

You don't have to register! Just follow the post every Friday, starting today.


Monday 25th of October 2021

I am on no social media sites but Pinterest but would love to participate in your 4 week challenge!? I have done the first week challenge but can not seem to find weeks 2-4 on Pinterest? I just moved from a cold winter climate to a much milder climate and think perfect time to do a closet and wardrobe challenge.

Megan Kristel

Monday 25th of October 2021

Hi! You can find everything right here:


Sunday 5th of September 2021

I love classic, dressy clothes, but I am retired and at home most of the time. It would seem sensible for me to change my wardrobe to a more relaxed, casual style, but instead last year I decided to dress most days as if I was going to work on casual day. I am a textile/fibre artist, and dressing up helps me to feel ready to create. I also feel much more confident about my appearance than if I wear typical “at home” clothes. My work is not terribly messy so that is not a factor. Because of this, I am thinking of skipping the pie chart exercise. Is there a reason why I should reconsider and do it anyway?


Saturday 4th of September 2021

My first time doing this.. thanks Megan! 14% work in gym 57% home activities 14% exercise 14% shopping/ visiting/ social My Pinterest: Ternullo/ lifestyle


Sunday 11th of April 2021

I seem to be a lot like Natalie in that I rarely wear pants (only yoga and real hiking.) Even though I dress on the dressier side than most, I never feel like I am over-dressed. Much of my wardrobe is relatively casual or at least can be used for anything from casual to lightly dressy -- depending on the accessories. On our almost daily walks, no one has ever complained that my skirt or dress looks horribly dressy.


Friday 8th of January 2021

I did your Wardrobe Challenge for the first time fall of 2020. I loved it! Please let us know what will be out of style next year. I'm disabled so I don't get out much. I tend to dress on the dressier side than most. I only wear skirts. Thank you for all the work you do for this blog!

Amy K Cornwell

Friday 18th of September 2020

70% work 15% gardening/ bird feeding 10% drinks and dinner with hubby and friend 5% reading, Forty years as a buyer for women's retail, retired for five years, retirement is very over rated! Purchased a small shop in a tourist town-work six days a week. And it is not a clothing shop! My closet would have you thinking I am classic and only wear black but I want to be colorful and wild with a few great pairs of shoes. This is my first time for the challenge.


Sunday 12th of January 2020

OMG, the struggle is real, and I’m 45 years old!! However this wardrobe challenge is very cool. Have been following for over 12 months, from Australia!! Gets a little confusing with our different season’s but catching the drift for sure. I’ve had a Pinterest account for ages, yet my wardrobe does not reflect what I now understand is my style, what have I been doing ???I’m pretty sure this challenge will reveal quite a lot... looking forward to it. Thanks, and think you’re amazing


Friday 10th of January 2020

Something that i started is using the Life Cycle app. It tracks where you go and creates a sort of pie chart for the day, the week, the month, etc. It is awesome. It logs where you go automatically, though sometimes you have to tell it the actual location, i.e. it uses GPS and sometimes there are multiple places that you could be, so can edit it to choose where you were. You also fill in what you were doing, although it automatically records “work” “commuting” “home” etc, but you can say you were “shopping” or “visiting” etc. I strongly encourage everyone to check it out. It’s not only insightful, it is FUN!

Megan Kristel

Saturday 11th of January 2020

WOW! What a great idea! Thanks!


Wednesday 6th of March 2019

Good Morning - love your website Meg and thanks so much for putting together this challenge. It’s my first and I was excited to do the weekly graph and Pinterest board. For no particular reason I’d been working on a Style Pinterest board and so glad it now has a purpose! I don’t know how to attach it here to share but upon review it has a clear theme; minimalist, monochromatic, neutral colors, pointy toe heels/ flats. This was especially interesting to me because I have tons of scarves that I never wear.

I spent decades in the corporate world and based on the volume in my closet, my head must think I’m still there. But I’m not. For the last 8 years I’ve worked from home and see clients in my home office. I could wear the exact same thing everyday and no one would know the difference. Several times a year I attend corporate business meetings which are trending to a more business casual vibe. My graph is below. This exercise really helped me focus on what I do and where. Thanks so much Meg! 80% home office 10% professional meetings 5% dress up - symphony, cocktail parties, special dinners 5% casual weekend

Mrs Jackie Rowley

Wednesday 12th of December 2018

Hi Megan love your site, my problem is I have a wardrobe full of outfits for evening outs ( not Posh ) holidays in France (not summer September time ) dresses expensive Jeans and Expensive knitwear for weekends away. And not enough everyday suff. I am retired 64 but occasionally work in our own buissness look after Grandkids ,shop meet friends for Coffee and have dressy/casual nights out for meals,

I havent a clue where to start please help what should I keep in my best /going out wardrobe/holiday wardrobe, and my everyday wardrobe.

Best regards Jackie


Tuesday 25th of September 2018

Dear Megan, I am 74 years old and fully retired, when I worked for a corporation I had no problem knowing what to wear, now I find myself being rather sloppy! I started a capsule wardrobe and purged my closet big time, and it not very interesting. I purposely have not gone out to buy anything new until know my style and I know where to start. I have used Pinterest and I am now finally seeing a pattern, I’m thinking that I am a classic casual. I am very excited about going through your challenges. Thank you so much!


Wednesday 24th of January 2018

I work at home half the time in old, stained sweatpants and an REI pullover from 2002, and in an office half the time, trying to fit in with consultants who dress pretty formally, in expensive, fashion-forward clothes. Most of them do not have children and shop or get manicures for fun. When I'm not working, I like to exercise and spend time on the floor with my 3 young kids. So breakdown: 50% casual, 30% professional, 20% athletic. I enjoy expressing my creativity through my clothes, but right now, I don't have time for it. Maybe a more edited wardrobe would help me dress faster and feel more pride in what I'm wearing. Here's my board. I dutifully deleted items that didn't feel special to my style, so now, everything here I really like.


Wednesday 24th of January 2018

Finally going out on my own (career-wise) and need to get my wardrobe up to speed. I'm working from home, so finding myself in pajamas WAY too much. LOL. Here is my pinterest:


Tuesday 23rd of January 2018

OK I am playing catch-up a bit. Here is my board: No surprise here, but a lot of my pins are from this site!

In lieu of a pie chart, here's my breakdown:

20% of my week working in a creative office 10% of my week working from home 14% of my week lounging at home, playing with my daughter at home 40% sleeping (I love my sleep) 4% dates/going out with friends 9% Running errands or casual weekend activities with my family 3% gym


Friday 7th of January 2022

@Lauren, I like your style! thanks! I have many of the same exact pins, but I have found some more to pin! Yay!

Christie Gilmore

Wednesday 17th of January 2018

Thanks for doing what you do!! Happy to try this 4 weeks challenge! (Who doesn't like a good challenge to start the year?) Once we have a nice big board of styles we like, are we supposed to know how to edit and shop? I am good at pinning but not at then determining how that should inform my decisions!

Megan Kristel

Wednesday 17th of January 2018

Hey Christie, We'll get to that in the next few challenges. The first thing to do is pin all the things you love and complete the lifestyle diagram without thinking about how to edit or shop just yet;)

Neen James

Tuesday 16th of January 2018

I have done your Style Challenge twice and loved it (and both times felt inadequate that I couldn't do the weekly activities and would get a little overwhelmed with a busy travel life and schedule, I LOVE the 4 weeks to a better wardrobe context and takes the pressure off those of us crazies who like to meet deadlines for accountability. I am rarely on Pinterest anymore but do love my boards, my style is still ridiculous shoes with everything :) - a great outcome of this challenge was donating so many of my unused, barely worn clothes to others who can enjoy them. Thanks for all you do and this new look and feel of the site and blog is awesome! Mint green suits you.

Megan Kristel

Tuesday 16th of January 2018

Thanks Love! I think keeping the challenge on the blog will streamline it for all of us!