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The 2019 Dressed for My Day Challenge

Building a Wardrobe
June 1, 2019

Happy weekend, gals! Do you have big plans? Or maybe, like me, you’re just working around the house and fitting in a fun moment here and there. I hope you’ll also grab something cool to drink and visit with me a few moments. I have an invitation for you! I’d like to invite you to join me in the brand new 2019 Dressed for My Day Challenge! Curious? Keep reading!

What exactly is the Dressed for My Day Challenge?

First of all, you can download all the details of the Dressed for My Day Challenge here.

The Dressed for My Day Challenge is a fun way to level up your personal style. It’s totally optional. I’ll continue to post my normal fashion inspiration and tips posts each day. But I’d love for you to join me in 30 days of daily challenges that will help you master some of your personal style struggles.

The 2019 Dressed for My Day Challenge is open ended so that you can choose the challenge that best suits your lifestyle and current needs. You can choose from the 5 challenges listed below or create your own. Just select or create a style challenge that will help you move from where you are today – style-wise – to where you’d like to be at the end of the month.

What’s your personal challenge? “I want to…

  1. ___ put more energy and effort into my appearance each and every day.
  2. ___ mix and match my current wardrobe more creatively.
  3. ___ consistently wear clothes I enjoy and look my best in.
  4. ___ dress appropriately but beautifully for a new season of life.
  5. ___ dress in a way that helps me influence others positively and engage gracefully.
  6. ___ or create your own personalized challenge!

Participate in Daily Challenges

Now that you’ve identified your personal 2019 Dressed for My Day Challenge, you can select the daily challenges you want to take on (Download the full list of daily challenges here.). You don’t have to do these in a particular order. Depending on your wardrobe and your personal challenge, you may want to skip some days or shift the daily challenges around to fit your personal calendar.

However, for the purpose of posting in the private Facebook group (more on that in a minute) and Instagram, I will be focusing on one particular challenge each day, according to this calendar. You’ll find a printable PDF of the challenges plus all the other information here.

Be a Part of the Community

Let’s make this fun! AND let’s help each other by providing accountability, feedback, encouragement and community. You can participate in the challenge through one or more of the following:

  • comments in the blog posts
  • a free, private Facebook group just for this challenge
  • Instagram hashtags (#dressedformydaychallenge)

If you’re not on Facebook or Instagram, your participation will admittedly be limited. But you can still tell us about how you’re doing with the challenges in the post comments. I’ll be asking you every day in my posts.

But if you are on Facebook and/or Instagram I highly encourage you to join the Facebook group and use the hashtags. It’s going to be so much fun!! And the purpose of all the participation is for us to have an authentic and safe community for genuine encouragement, gracious accountability and pure enjoyment.

Join the Private Facebook Group

If you’re on Facebook, I invite you to join the private DFDMChallenge Facebook Group. You’ll need to ask to be allowed into the group by answering a couple of simple questions. The group is private, only open to women who are participating in this challenge. I’m the sole administrator, so I’ll be vetting every application. My goal is to create a safe environment for this challenge.

  • Introduce yourself once you’re in the private group.
  • Each day check in for challenge updates
  • Post your photos, questions and comments in the Facebook group in each day’s discussion stream.

Participate Via Instagram

To participate through Instagram, simply tag all of your selfies or photos that pertain to the daily challenges with the hashtag #dressedformydaychallenge. Also, check out the other posts in that hashtag feed each day and leave positive comments on them and “like” them. Remember, this is not just about posting your photos. It’s also about community. We want to encourage and support one another by engaging in each other’s posts.

Note: your photos do not have to be “fashion selfies.” They can be photos of you with your kids, your husband, etc. As long as they picture you completing one of your challenges, they are perfectly appropriate to use. Just include the hashtag #dressedformydaychallenge in the caption or in the comment section so it will show up with all the other tagged photos from other women.

Note: your account will have to be set to public for us to see them. Or you can invite me and others to follow you and those who follow you will be able to see your photos. Follow me here @Dressed_4_my_Day and ask me to follow you if I don’t already. I’d be glad to follow you gals!!

Participate in the Comments

The final way to participate is to leave comments at the end of my blog posts sharing your questions and progress with the daily challenges. This is the most limited form of participation, but I will be posting about the challenge every day (except Sundays) during June. And I will value your participation.


If you have questions about the challenge, please ask them in my Instagram photos (@dressed_4_my_day), in the private Facebook group or on the blog in the comments of any June post. That way other women can learn from the answers to your questions as well. But I think the download PDF may answer a lot of your questions.

Did I mention the prizes???

Three prizes will be awarded to participants who stand out for doing the following:

  • participating in multiple challenges
  • showing up consistently in either the blog comments, the Facebook group or the Instagram hashtags
  • engaging with other participants in a way that is gracious, encouraging and congenial.

Also, there will probably be other “doorprizes” awarded to lucky participants throughout the challenge. Watch for those!!

Let’s Get Started!

I encourage you to download the Challenge packet with all 30 daily challenges here. But each Saturday I will provide the next week’s challenges, too.

Here are the challenges for June 1-8:

  1. Today is National Nail Polish Day. Yep. It really is. Make sure your nails are polished a color (or neutral) that makes you happy, works with your wardrobe and looks fresh and contemporary. Post a pic on social media with the hashtags #nationalnailpolishday & #DressedforMyDayChallenge. (A,D,E)
  2. Select a primary piece of clothing – dress, jacket, pants, skirt – that you will wear today and tomorrow, but style it very differently each day. (B,D,E)
  3. Today is actually National Repeat Day. Yep. It really is. You can share your photos of yesterday’s outfit and today’s in which you repeat one item with the hashtag #NationalRepeatDay as well as #DressedforMyDayChallenge. (B,D,E)
  4. Think about someone you know personally whose style you admire. Interview her in some way, asking her how she puts her outfits together, where she shops, what her style philosophy is. Go ahead! She’ll feel flattered and share gladly. Share a photo of her (with her permission of course!) and or just tell us about your interview. (A,D,E)
  5. Begin a Pinterest Board called “Dressed for My Day Challenge.” Go window shopping on a favorite retailer website or two (check out my shopping pages in the top menu), looking for clothing to fit your season of life and style. Begin to collect photos/pins of outfits that inspire you to meet your personal challenge. (A,B,C,D,E,F)
  6. Today is National Eyewear Day. Consider how your eyewear affects your appearance. Even if you just wear reading glasses, put them on and look in the mirror or take selfies. If you’re not super impressed with what you see, begin looking for new eyewear. Even if you shop Target or Walmart, you can find fashionable eyewear of all kinds to enhance your appearance rather than detract from it. You might be interested in this post I wrote about reading glasses. (A,C,D,E)
  7. Wear jeans or jean shorts today, but dress them up with fresh accessories or shoes. (A,B,C,D,E)
  8. Yes, it’s Saturday, but you can still wear a dress. Choose a simple one for daytime or put on a pretty maxi skirt or dress for the evening. (A,C,D,E)

Let’s get started!

Alrighty then! Please give me your questions. I know this may seem a little complicated right now, but I think once we get going it won’t be.

Also, rest assured, I will actually continue to post as normal here on the blog. So if you opt not to participate in the Dressed for My Day Challenge, you’ll still find style inspiration and tips here every day except Sunday. In fact, I have some great posts lined up for this month, including a summer style collaboration with Susanne at Thompson Hill. Yay!

Blessed for My Day

How do you handle change? I like to think that I welcome change and even desire it. But the truth is that even good and solicited changes can cause us some frustration and tension. Change is hard.

If you are facing changes – at work, in your family, at church, in your neighborhood, regarding your health, whatever – rest in the fact that God is in the changes. He is not taken by surprised or caught off guard. God is steady and never-changing, and yet He is also the master of change. He incorporated change into our day, our calendar and our bodies. Lean into Him and ask Him to help you adapt to the changes you are experiencing.

Blessed be the name of God forever and ever,
    to whom belong wisdom and might.
He changes times and seasons;
    he removes kings and sets up kings;
he gives wisdom to the wise
    and knowledge to those who have understanding;
he reveals deep and hidden things;
    he knows what is in the darkness,
    and the light dwells with him. ~ Daniel 2:20-22

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xoxo, Kay
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14 thoughts on “The 2019 Dressed for My Day Challenge

  1. Hi Kay! I am going to do my best to participate in the daily challenges. This morning I ordered a stripped midi dress and the pink graphic tee you shared earlier this week, from JCPenney. Those are the last pieces of clothing I plan on purchasing for the warm months because I really don’t want to add more clothes to my closet. In all honesty, I’d like to remove some pieces for various reasons. One of the reasons I continue to put off taking action is because there are numerous transitional tops and bottoms in my closet. I know if I removed those pieces, my closet would not be so full. I also know there are tops, in particular, that really aren’t right for me, but I haven’t pulled the plug like I need to. It’s time for me to stop making excuses and start taking action. I plan on polishing my toenails tomorrow morning, so I hope that will count towards the polish challenge. If I do them now, 12:30p.m., there is no doubt in my mind I will mess them up. Another great BFMD!

    1. Hi Ginger. Yeah, you can mix the days of for the challenge as needed. No problem. And in fact, there are a few days when the challenge is to REMOVE some things from you closet! Ha! So that may work well for you. Really, just make the Challenge work for you. It’s not meant to add frustration to your life in any way. 🙂

  2. Thanks for sharing your slice of life online and orchestrating a monthlong fun challenge! Just finished painting my nails-Sally Hanson Complete Salon Manicured in Fruity Petutie. So, I am now stoked for the challenge of mixing up my current wardrobe pieces to inspire multiple versatile outfits. While I’m not much of a public poster/sharer, the private FB group page should work just fine—- guess we’ll see.

  3. I’m always amazed at the countless national (fill in the blank) days! So today, in honor of National Nail Polish Day, instead of polishing my nails, I applied Impress Nails and love them! They are already gel polished, and look so real. They’re super easy to apply, and don’t ruin your natural nail. Generally, they come with 1-2 complimentary embellished nails if you like adding a little bling.! I’m not on social media, so I can’t provide a photo; but I chose a beautiful blush pink color that will compliment most anything I wear!

    1. I’ve heard great things about those. I’ll have to try them. I’m glad you’re participating in the challenge. We’ll make it fun!

  4. I need to paint my toes for summer, and this will give me the motivation to do it. My mother always liked to wear bright color on her nails and was always so proud of them. After her stroke, she was unable to do that. When she passed away 10 years ago, my sister painted my mom’s toes red for the funeral (even though mom never painted her toes, lol). No one but family knew, but it was a quiet tribute to something she loved to do. From then on, I have only ever used red to paint my toes.

    1. Thanks for sharing that Linda. Such a sweet tribute to your mom. I love that. It’s the little things that often most help us through grief. Lovely. Now, get those toes polished! ???

  5. Love the idea of the challenge. My first thought was to join in, but I will be out of town 4 days this week. Then I have two bouts of company coming afterwards. Maybe another month lol

  6. Wow this looks so fun. Thank you for putting together…you put a lot of work into this! I am behind already but will try to get with the program and post something soon. Thanks for all of your hard work on this and everyday. I look forward to reading your blog.

    1. Great! I’m glad you’re joining us. No need to worry about being behind. I don’t want this to be anything that stresses you out. It’s meant to be fun and flexible but hopefully also a little challenging. Enjoy!