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Join Me In a Style Sister Challenge!

August 25, 2023

Hello, Sister! I hope you don’t mind me calling you that. Here at Dressed for My Day I try to encourage and inspire women over 50 to step out with a little style each day, but also feeling authentic and like the best version of ourselves. And I feel like we’ve developed such a warm and fun community of women who are trying to do just that. So I thought it would be fun if we spread the joy by taking a little Style Sister Challenge. I’ll explain…

Style Sister Challenge

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The Style Sister Challenge is much more about being sisterly than it is about good style. You see, I’ve discovered, in my five and half years of blogging in this space, that many women over 50 are struggling to feel good about their bodies, their personal style and their ability to look modern and beautiful in this season of life. I’m much more concerned about getting those women back on their feet than I am about getting their feet into pretty shoes. (Although pretty shoes sure can do a lot to boost a woman’s self-confidence. Just saying!)

white linen blazer
me and my mom Louise in this video

And I’m so blessed that almost every day at this point, I hear from women who tell me that this website and my YouTube channel is helping them to do just that. They email me or leave comments saying that they (maybe you!) have started putting in a little more effort and pulling together a real outfit rather than just putting on yoga pants and a t-shirt and calling it a day. Or they say they’ve started building a real wardrobe that mixes and matches rather than just accumulating odds and ends that frustrate them. And they say they’re enjoying getting dressed for their day and the compliments coming their way are quite enjoyable, too.

Donna and Kay
DFMD reader Donna and me in this blog post

But I’ve also noticed that it’s not just older women who need a little inspiration and information. Younger women really look to us older ladies so much more than we may suspect for a little affirmation. They’re watching you! And they love getting a little grace and kindness from you.

Mom, Me and Abby in Talbots Fashions
my daughter Abigail, my mom Louise and me in this post

We live in a competitive culture, unfortunately. But there’s no place for competition here. We need to be encouraging the women around us, whether they be older, in our same season of life or younger. And we don’t need to assume that our polished, poised friend or that super stylish woman we see at church each week doesn’t also need a little sisterly kindness, too. She absolutely does.

Me and Blake at Kenwood Talbots
my Talbots stylist and friend Blake and me in this blog post

So let’s you and I do our part to spread that joy even further. All around us are women who need a little encouragement, a genuine compliment and maybe a little updated information. They want to get dressed for their day and look current and classy, but honestly they’ve just lost their way a little. It’s happened to most of us. So let’s reach out and give them a hand.

Kate Linen Pants and Parke Linen Blazer
me and my stylish friend Jamie, who’s also a reader here and a manager at our J.Crew, in this blog post

Want to take the challenge with me? Here are a few suggestions for how we can be an encouragement to some sisters:

  1. Compliment a younger woman whose style you admire. Trust me, it’s not just older women who need some encouragement. And when we start trying to notice some younger women and give them a little kindness, it will actually help us to appreciate their contemporary style more. Our minds get broadened and their hearts get encouraged. Win, win!
  1. Compliment a woman who is obviously making an effort go get dressed for her day. Sure, compliment the truly stylish woman, too. But when you spot someone who may not be the most stylish but she sure has made an effort, affirm her efforts. Keep it sincere and simple. Maybe say something like, “You look so pulled together today” or “I love that color on you; it really brings out your eyes.”
These jeans are generally going to look best with a close fitting top to keep the outfit proportionate. Which proportions am I referring to? In your outfit it is best to have some of your outfit fitted and some of it more relaxed, especially if one of the pieces is very voluminous. So to balance the volume in the jeans, wear a more fitted top.
wide leg, full length jeans // effortless jersey stripe square neck top (size down; wearing a Small) // necklace // belt (wearing m-l) // convertible shoulder bag // similar sneakers (GREAT more economical option)
  1. Graciously encourage a young mom with kids in tow. Young moms need lots of grace. Do you remember those days? I always loved it when an older woman took notice of me and said something kind and gracious. Be careful that your compliment isn’t backhanded. Know what I mean? Keep your words truly uplifting and gracious, something like, “You’re doing a great job, mom” or “You sure do have a beautiful family, and I can tell they love their mama!” Most importantly, let her know you see her…not just her kids.
  1. Host a casual luncheon or brunch or tea for a few women friends. Watch one of my YouTube videos together and discuss among yourselves, keeping the conversation gracious and uplifting.
  1. Leave a positive and encouraging comment on a social media post of another woman. Say a little more than, “I like that.” Get friendly and strike up a conversation. Let her know you “see her” and value what she has shared.
  1. Compliment a peer whose style you admire. Take this one a little further. Instead of just telling her you like her dress (again!), share with her that she inspires you. Tell her you appreciate her style. Ask her where she learned to put herself together so beautifully. Ask her if she has a style muse or where she enjoys shopping. In other words, let her know you see her.
Navy Chinos and Graphic Tee
my daughter Abigail in an old post
  1. Talk openly and graciously with a younger woman – maybe a daughter, granddaughter or niece – about your own body and self-concept issues and how you’ve overcome them…or at least how you’ve made progress. Let her see your own vulnerabilities, but also give her hope and encouragement.
  1. Share my blog and/or YouTube channel with some friends. I love it when you share Dressed for My Day with friends. Word of mouth is always the best way to grow this community. Tell them why you enjoy it and what they can expect.

So will you take the challenge, sister? Let me know your thoughts! I’m still in London, but I’d love to hear from you today.

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Blessed for My Day

Encouragement is such a priceless gift, so why do we not give it more often? It’s value is immeasurable, but it really costs us so little to give. I’ve found that the best and most inspiring encouragement is not the admonition to do something differently or better, but the affirmation that one is on the right track. That doesn’t necessarily imply that the other person is getting it exactly right yet. Maybe they have a ways to go. But just telling someone that they are moving in the right direction can be so motivating.

How can you encourage someone today who is obviously trying? Consider how differently you receive encouragement that is actually criticism or instruction cloaked in cheerful words in contrast to how you are motivated by kind affirmation that you’re moving in the right direction. Think about what truly pushes you forward. And also take note of “encouragement” that feels more like impatient prodding. How can you give truly motivating encouragement today?

Therefore, encourage one another and build one another up, just as you also are doing. ~ 1 Thessalonians 5:11

xoxo, Kay
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18 thoughts on “Join Me In a Style Sister Challenge!

  1. I think this is a wonderful reminder for me Kay! I live in a 55+ community and I’m surrounded by women in this season of life. I see a lot of them around the community and in the neighborhood. And when I talk to them, I often forget to compliment or encourage them in some way. This is a nice reminder to insert that in my conversations.

  2. Fantastic idea and I will do it. I have some young women at work and also my 93 y.o. mother in law. We are going out to dinner together early Sunday evening and she always makes an effort. I will be sure to mention how nice she looks!!

  3. I loved this post—I am guilty of thinking someone looks extra cute when I see them at church and I don’t make a point to tell them; I need to be better at that! Thanks for the reminder and encouragement! Enjoy the rest of your trip—it looks fabulous!

  4. Dear Kay, This little challenge or yours is a great idea and really has my mind spinning. You gave some good tips to connect with other women instead of insulating ourselves when we’re out and about. I think in general women used to be more like this but the past few years gave us reasons to cocoon ourselves. Thanks Kay!

  5. Love this post! We just moved into a new state, new neighborhood and now a new church. I’ll look for ways to reach out to others in this new season.

  6. Hi Kay and Ladies, what a Beautiful Post Kay and your BFMD , Absolutely Right! It costs nothing to be nice but absolutely right you have to be Sincere and mean it, which I always do ! and Kay you are right everybody even those ladies who we think are super confident , deserve to be complimented on how well they are looking/doing . Thank you for all your Inspiration Kay , you really are a Gracious and Beautiful Lady ❤️Xx

  7. Yes! Yes! Yes! I needed these reminders and I know the women around me need to be encouraged! Thank you for these specific ideas….I’m on board!

  8. Kay, I just love this! This makes my heart so happy! I will take the challenge! Thank you for all you do to make the world a better place 💕 God is using you as He expands your territory!

  9. I compliment stylish women but will give words of encouragement to those who are not stylish but trying. Sometimes older women still wear dated outfits but they are trying and just don’t keep up with trends. Instead of thinking in my mind how dated the outfit is, I will look for the positive. I always love Blessed for my day and how you explain it.

  10. Thanks for such wonderful words to me! You do lift my spirits and make shopping a breeze for me. I wish everyone could feel how much better your day goes when you do put the effort in to ” dress for your day” no matter what you are doing. I feel depressed if I keep my jogging clothes on all day- hat hair and all! I compliment people at work, but will try to enlarge that window of compliments! Thanks for all you do Kay!

  11. Kay, you are so right about the need for us women to uplift one another. Many times I’ll be at the grocery store or some place and see a woman with a beautiful outfit or who just looks great, and instead of just thinking it to myself I’ll say to her, “I love that dress!” Or something similar. It’s so fun to see her face light up with the recognition that someone sees her! It makes the giver of the compliment feel great too, so a win win!