Join Our Fall 2020 Wardrobe Challenge!

It’s that time of year when we come together and begin our Fall Wardrobe Challenge!

I host our FREE four-week Wardrobe Challenge every January, March, and September to get our readers ready for the new season

Our Wardrobe Challenge has become the cornerstone of this site, creating a community of lovely women from all walks of life, bonded together by our love of classic style and our desire to look and feel our best. 

The challenge is based entirely on the process I used to help my personal styling clients. I broke it down into a series of activities designed to help you (1) define your personal style, (2) edit and organize your wardrobe, and (3) begin to build a wardrobe of clothes you can’t wait to wear. 

Because we are constantly evolving, this process is designed to be done seasonally. Each time you complete it you’ll have made a new discovery, and gain further clarity around your personal style. AND, you’ll force yourself to tidy up your closet 🙂 

The Well Dressed Life Fall 2020 Wardrobe Challenge

 

Our Fall 2020  Wardrobe Challenge starts on Friday, September 18th. 

Here’s what some of our participants have said, taken directly from our Private Facebook Group:

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!

 

This has been great. The big eye opening moment was when I realized that my wardrobe didn’t look anything like my Pinterest boards. The result of shopping without a plan, looking to brighten myself 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.

 

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 appreciate 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.

 

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!

What You’ll Learn

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

  • Clearly understand your personal style and wardrobe needs.
  • Start your day with a functional and well-organized closet.
  • Have an outline of the pieces you’ll need to have a wardrobe you love.
  • TONS of personalized support in our Private Facebook Group.

Ready to get started? 

Here’s How it Works:

The challenge starts on Friday, September 18, and lasts for four weeks. 

Every Friday, a new set of challenges will be posted right here, on The Well Dressed Life, and in our Private Facebook group. Within the post, you will find two challenges to be completed before the next week. 

We move quickly on purpose. It keeps you engage and helps you make decisions quickly. But if you get busy or distracted, you always have access to the information. 

What You’ll Need

It’s helpful to have a clothing rack, this is the one I use

You May Also Like
The Fall 2020 Wardrobe Challenge: Week 1

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 from Amazon

If you receive an email from The Well Dressed Life in your inbox everyday, you’re all set. To get on the list, simply fill out this form here

For even more support, join our private Facebook group and 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. Many readers do it religiously every season!

A Little About Me (in case you’re new!)

Under $20 Holiday Ready Sweater

After college, I started my career as a women’s clothing retail buyer for large chains and private boutiques. Before I started my first company, my last job was as a buyer for the home-shopping powerhouse, QVC.

In 2007 I left that job 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 we stepped in.

I’ve personally helped thousands of clients navigate the often overwhelming world of fashion and retail, working within their style, with all sizes, body shapes, and budgets.

Three years ago, I stepped away from our 1:1 services to focus on building our online business. Connecting with other like-minded women has always been my absolute passion. 

Today, this is my full-time job. I’m so grateful I’ve been able to continue to provide expert advice and insights in our daily posts and through these challenges.

I do not represent a company and am not sponsored by any brand or business. All of my recommendations are solely based on my knowledge and experience.

I’m a working mom to three girls, ages 13, 10, and almost 2. I use my experience as a buyer, personal stylist, and busy modern woman to frame my advice and recommendations. 

It’s About You

Society puts an often unbearable pressure on women to look a certain way. Daily, we’re inundated with unrealistic images of what we’re “suppose” to look like, which not only chips away at our self-esteem but also provides zero guidance to help usual women shop and get dressed. 

Turning 40 at the end of last year has helped me care less about what I’m “suppose” to be and more focused on who I am. 

This challenge, and the contents of my site, come from a place of wanting you to feel confident and empowered as you are.

I encourage you to use the next four weeks to focus on YOU. Dive right in, ask questions, and get to know your fellow participates, who you’ll quickly discover are the friendliest and most supportive group of women. 

My goal with this challenge is to give you a clear understanding of what you like and what will work for you so getting dressed becomes an expression of who you are and not a chore. 

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

All I ask is that if you enjoy our content, please share it with your friends! 

Tell me below: who is joining us, and if so, is this your first time or have you done it before?!

 

Join Our Fall 2020 Wardrobe Challenge!

81 thoughts on “Join Our Fall 2020 Wardrobe Challenge!”

  1. Just finishing up a simplicity workshop that also encourages a capsule wardrobe! Excited for this to be my next step! First time doing the challenge!!

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  2. Sounds like this is just what i need😁. Im 67 and retired and trying to find my “new” image in a casual ACTIVE retired community.

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  3. I plan to participate – This will be my first challenge! I’ve personally been struggling with my wardrobe because of some significant weight gain and finding it difficult to dress my newly acquired and not so welcome curves. Thanks for all you are doing !

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  4. First time and I am looking forward to it. I think I know my personal style but I am sure I could improve based on what doesn’t get worn but takes up space in my closet

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  5. I am excited to start this journey. I am a young 68 year old, 5’6” at 170 pounds. I am in the process of losing weight (of course) so I’m looking for a new game plan with my outfits. I prefer classic styles but will add a little twist to make it me. Thank you for all the great information, I am so glad I found you !

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  6. This will be my first time doing the challenge. I am really excited to get started. I feel as though I connect with you and your style very well, as I too am a mom of 3, although I’m in my 50’s, my oldest is 18 and my youngest is 13! I recently re entered the working world in a business casual office setting, I love classic style dressing and would love to learn more about finding what works fir me to look polished, stylish and put together both at work and at play. Thank you for all you do for us ladies who need your professional advice!

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  7. I participated in January, very refreshing, loved it. I turn 60 this year but don’t feel or think I look my age, I’m a business owner, and a very active person, your posts, suggestions are very helpful to getting my style with comfort. I’ve even purchased a few items and I got to tell you originally I was skeptical but loved what I got and wear them often interchangeable with my current wardrobe.
    Thank you

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  8. Hi I have done this challenge before its brilliant and I can’t wait for March 13th.
    I have a classic style (Kate Midfleton) although in my sixties this style works really well.
    I think you do a fantastic job Kristel I have looked at many other sites and yours is by far the best .
    Thank you

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  9. This sounds like a great idea, and I would love to participate! I’m currently home on maternity leave (going back to work in June)- do you think it would still be beneficial for me to participate or should I wait until the next challenge?

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  10. Joining for the first time and couldn’t be more excited! I know what pieces I like, but my closet is full of stand alone items. I need help in putting a wardrobe together that can use classic, basic pieces for multiple uses. Making outfits is my goal. Recently retired and a grandmother of 4, I now have the time to work on myself.

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  11. I have been reading your posts for a couple of months now. I am retired now and need to change my wardrobe out, I am 62 years old but I don’t feel old and I do not want to look/dress old. I like a classic look but feel that it can look old and frumpy sometimes. I need to be able to have a core closet but still be able to add in fresh current ideas without feeling like I am trying to hard to be younger than I am. I have enjoyed your articles and I feel out of the other 2 sites that I have been viewing, I like your style the best. How does someone at my stage in life do this with her closet? Is your site geared for someone who is more your age? I feel my wardrobe needs to be more of a casual wardrobe because of being retired, but I also need some classic dresses/slacks or skirts/tops for times when I need to attend a wedding or a dressier event. I happen to like moto jackets/animal prints/wedge heels and kitten heels but wonder are these items that I should not be wearing anymore? I would appreciate any feedback that you could give.

    Thanks

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  12. I participated in January and will do so again. The eye-opener for me last time was creating a circle graph of how I spend my time. I found that I was buying things for a very small slice of the “graph pie.” So I had clothes I hardly had an occasion to wear and a hard time getting dressed for my daily activities. This website and FB group is a terrific resource.

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  13. This will be my first time doing the challenge also. I am looking forward to discovering my own personal style and gaining some confidence in my own uniqueness and inner beauty. I want my wardrobe to reflect that beauty and confidence.

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  14. My first time and I am ready to get started. I often go to my closet and do not feel I have anything to wear. Eager to find my style so I find myself.

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  15. Hello:
    This will be my first wardrobe challenge. I have found it incredibly difficult to shop and build a functioning wardrobe that suites my needs. I am retired, in my 50’s, have a high school-age daughter, and live in Scottsdale, Arizona. I realize your approach is focused on East Coast seasons but the concepts are universal. I have thoroughly enjoyed your posts, spot-on recommendations and pearls of wisdom. Looking forward to getting started!

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  16. I did this challenge last year when you first opened the FB page and really had great success. However, since then I’ve fallen back into old habits so I’m joining the March 15 challenge. I am 64, semi retired, self-employed and I live in jeans.I also live in the desert where layers are essential because we basically have two seasons in one day during 4 winter months and sweltering heat 8 months out of the year. My goal is always to dress age appropriately but not look frumpy!

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  17. Here we go again! Did a closet purge with your challenge last year. Ready to add the right pieces now. I’m 70s, retired, live on the Gulf Coast in Florida.

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  18. This is my first time. I love fashion and buy too much from the clearance rack that end up going to thrift shop unworn. Now in my 50’s, I am learning why those items were never a “bargain”. I live in Southwest Florida where the uniform is tank tops and shorts or leggings with oversize T-shirts. When it’s 90 degrees and 90% humidity 8 months out of the year, its a challenge to polish, elegant and be comfortable. Layering is mostly not a option. I end up a hot mess. I am hoping to find options and ideas that will work. Thank you.

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  19. Hi, this will be my third challenge. I didn’t put as much effort into the last one, not so busy now, so ready to go!
    I have found the purging of clothing to be most helpful. And it’s gotten easier to do!

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  20. This is my second go around. I enjoyed the first time and I am so looking forward to this challenge. Two reasons for my excitement, I turn 72 next week and I lost 32 lbs last year due to a great diet plan. Few of my clothes still fit properly, so with few exceptions, I am working with a clean slate. Your clothing choice and pairings helped me put outfits together that are age appropriate and easy to shop for. When I went to Nordstrom I found myself walking in circles because I don’t know what designer I am looking for I just wanted a blouse. The very next day you featured a blouse from Nordstrom that was exactly what I was looking for, I ordered online and I love it. Thanks for all you do, I look forward to receiving you wisdom each and every day.

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  21. This is my first time and after reading your post completely through 4 times, I’m not sure what I’m going to be doing during the challenge. Purchasing wardrobe items recommended as timeless pieces for all ages/body shapes, etc? Am I trying to build a basic wardrobe with pieces by a certain date? I’m sorry, if someone could answer or explain this to me, I would be forever grateful. Love most of the pieces shown, just don’t know what I’m supposed to do. Thank you.

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  22. I participated in January and can’t want to continue in March. I feel like I have learned so much is just the past few weeks. When looking at clothing I can ask myself “will this improve my wardrobe”? Most of the time the answer is no. I have also realized I need to expand the universe of stores I shop in. My old stand-by are just not cutting it anymore. Thank you, Megan for your guidance.

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  23. This will be my first time since I only found you a few weeks ago. I am 61 and mostly dress traditionally with a lean toward casual preppy.

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  24. Hi, I’ll be joining. I didn’t do the January one as I felt that I wasnt ready after doing the September one. Here in the uk our seasons tend to fall into autumn winter and spring summer. So doing the challenge September and March are perfect for me. We’ve had a really long wet winter and I can’t wait to start going through my spring summer clothes and packing away my boots and jumpers. Roll on spring. I’m looking forward to the challenge.

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  25. Just discovered you about a month ago. Getting emails and joined Facebook Group. This will be my first time participating. Looking forward to it!!!

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  26. Count me in! Loved the January challenge. Purged a lot of items from my closet and made some organizational changes. I have added some great pieces to my wardrobe based upon the recommendations and inspiration from Megan. Looking forward to the next project!

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  27. This will be my second challenge. Completed the January challenge after just being back to work from maternity leave. Looking forward to the next challenge!!

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  28. I’m going to join the challenge for the first time in March. I have a work style I love but really struggle with what I want outside of that environment…

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  29. Can’t wait!! Just found this group and can’t wait for the March challenge! I’m always stuck when it comes to a spring wardrobe so this will be great! Thanks for including me!!

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  30. Hi Megan
    This will be my third challenge and I am excited and ready. It will bring me into spring on time, instead of waiting until it gets here.
    Dee

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  31. This will be my first time. I think I know my style but have collected far too many things over the years that probably need to go. Very excited to start.

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  32. This is the first time joining and I’m very excited for this opportunity you have given me!

    Thank you my dear!

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  33. 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.

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  34. 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.

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  35. 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.

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  36. 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.

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  37. 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

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  38. 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!

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  39. 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.

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  40. 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.

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  41. 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

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  42. 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 🙂

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  43. 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.

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  44. 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!!

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  45. 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!!

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  46. 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!

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  47. 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!

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  48. 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.

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  49. Been watching and observing for the past several years always opting out because of…. you name the excuse and I’ve probably used it. My goal to downsize and simplify is out of reach if I keep adding random pieces of clothing to my closet. Buying more hangers and bins is no longer an option. The boxes of yet to be donated clothing that I packed up three years ago along with the out of season items in my storage room are taking up too much room in my life and my head. Its time to define my style, clear out what doesn’t work, stop wasting money on clothing that I don’t need and build confidence that my wardrobe choices represent my true style.

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  50. This is my first challenge, and I’m so looking forward to it! I’ve been a clothes hoarder for my entire life and have 5 different sizes in my closet!! I work for a company that has gone from corporate wear (suits) to casual to now working from home. In addition I’ve now lost 25lbs and am working on losing another 25!! I’ve always had a classic style but have lost my way and am just buying with no idea what looks good on my shape. I can’t wait to start my new direction!!!!!

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  51. This will be my 1st ACTUAL time doing this. I’ve signed up before but other things got in the way including total overwhelm when it comes to my closet. Now that I’m retiring I plan on tackling these fun exercises, not getting behind & creating a look that’s me!

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  52. I am participating again fir a second time. Just found several blazers that are outdated that I’ve replaced with the fabulous J. Crew sale our AMAZING leader and down to earth Fashionista, Megan, shared with us. I am recovering from surgery for 4 months, nearly immobilized for 6 weeks…but my left hand/arm still works.

    I love doing this as well as the camaraderie among ALL the amazing women I “meet” in our FB groups. Happy to “friend” some women if you have time/are still quarantined.

    This had been on of the best investments I’ve made in myself. Megan has the best tips, best price points for almost every item from clothes to skin care to a steamer…I wouldn’t miss this for the world!

    Enjoy!!

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  53. Hi, I am joining you on September 18, my first time. I am 76 yrs young and usually like to dress in slacks / and top jackets on Sundays for church. Looking forward to learning more

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  54. I plan to join the challenge. I don’t like to shop or choose clothing. On my own I would be plain. I want to expand my wardrobe and accessorize.

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  55. Hi All,
    I am excited to begin (again) and carry through to the finish!
    I do have a request though; at one point I had the wardrobe ‘list’ and now that I’ve followed the Well Dressed Life for several years, I can’t seem to get it again. Can it be posted on FB so I can print it off and compare with my own needs?
    Judy

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  56. Doing this fall wardrobe clean up/challenge for the first time! I’ve been a fan and member for several years now and I can’t wait!

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  57. I was hesitant to do this at first because I’m 16 weeks pregnant with what will hopefully be our final kiddo. However, after pulling out my maternity clothes, most of which were purchased when I worked full-time in a business professional environment and have gone through two other pregnancies, I’m realizing I need a plan for the next few months. If I’m not intentional about this, I’ll end up buying more than I need just out of sheer frustration. So, I’ll be doing the challenge to regroup and make sure I have the clothes I need to get through the next two trimesters and maternity leave!

    Reply
  58. This is my first challenge. I love you site. I just lost 20lbs and looking for ways to dress my new body. I am 61 years young and have had a hard time figuring what make me look young and not old. I got a friend to join me. So excited!!!

    Reply

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