It's so nice to meet you!
Get to know Kay...

What the Cool Girls are Wearing This Fall

October 13, 2022

Are you a cool girl? Hahaha! I think most of us women consider everyone else to be cooler than ourselves. Amiright? Especially as we get older, it becomes more and more difficult to really feel cool. By this time our kids have rolled their eyes at us so many times we’ve left all the cool vibes behind. And despite the fact that those same kids have generally come around again to seeing us as wise beyond our own estimation, we still feel pretty dorky when we get around the younger set. But let me whisper something in your ear, dear friend over 50. You are one of the coolest girls I know! Why? Because you’re still showing up and giving it your best. And you absolutely can wear what the cool girls are wearing this fall.

Wearing Sneakers with Wide Leg Trousers
similar pants // similar sneakers (more economical option) // belt // tank // denim jacket (plus sizes) // necklace // similar earrings // similar shoulder bag (more economical option) // similar bangle

Being cool is one of those things quite akin to “looking young.” If you try too hard, you miss by a mile. But who’s trying? Right? And that’s exactly why you are indeed so cool. Looking cool is that thing you accidentally fall into on your way to simply being yourself. And you and I know that’s all we’ve got left…being ourselves. Yeah, we’re still awkward and a little unsure of ourselves at times. But even that clumsy, last-straw self-acceptance is somehow endearing and, yes, cool to those around you.

Cool Girls are Wearing

I certainly wasn’t one of the cool girls when I was younger. We’ve got readers here who could attest to that. Ha! They witnessed my awkward middle school and high school years. I was taller than all the boys, flat chested and always had a perm in my hair (compliments of the high school cosmetology students at the school where my dad was a principal). Come to think of it. The only thing that’s changed from that list is that I finally figured out how to style my own hair…and then it thinned and went grey!

What the Cool Girls are Wearing This Fall

No, I don’t feel like I look much cooler these days than I did back in the 80s, when I truly did my best to at least look like I had it all together. Of course I don’t care like I did back then either. I’m not trying to impress anyone. I’m certainly not trying to attract a guy. I somehow managed to do that eventually, and I’m happily keeping the one I got.

I don’t have to walk down the aisle of a school bus each day lugging a huge French horn case and hope I don’t trip. I don’t have to walk through a cafeteria carrying a lunch tray that I hope I don’t spill, looking over the crowds and hoping for a seat amidst friends. And I don’t have to ask a guy friend to take me to our junior prom only to have him turn me down. Yes, that happened. And I didn’t go to that prom. Not cool.

What the Cool Girls are Wearing This Fall

It tickles me because some days it feels more awkward than ever to be over 50. Somehow my body doesn’t do the things it used to do so easily…like walk upright and bend down to pick things up and…have you even tried to skip lately??? And my face and hands and hair and upper arms and tummy…need I go on?…are all changing so rapidly! Yes, in many ways, when we get over 50 we feel just as awkward as we did in middle school.

What the Cool Girls are Wearing This Fall

And yet…at this age we can let the air out of that big, bossy, bad attitude a lot more easily than we could in our teens. We can remind ourselves that we have people who love us. We have accomplished big things. We have gotten through difficult things and gained a little wisdom along the way to share with others.

We’ve developed, too. Maybe we never did develop the body we envisioned, but we cultivated character and built a career and grew a family and accumulated friends and nurtured other lives and curated a life that counts for something. And when we put things in that perspective, those feelings of dorkiness and clumsiness and not fitting in…just dissipate and lose their power over us. Oh, to be able to pass that gift on to our daughters and granddaughters. What a gift that could be!

What the Cool Girls are Wearing This Fall

So I started writing this blog post with the intention of talking about what the cool girls are wearing this fall. You know…sneakers with wide leg trousers and a denim jacket and a I-know-something-you-don’t-know confident smile. But when I look at these photos I don’t see a cool girl. I just see me. And I know that, on any given day, I can feel less like a cool girl and more like a frump. No, I don’t generally feel like a cool girl.

Here’s the thing. I’m just a girl doing my best to show up with the best version of myself that I can muster up on any given day. Some days I knock it out of the park. Other days, not so much. I have moments when I feel confident and secure and pretty. I have just as many when I feel invisible or, worse, dorky and taller than all the boys.

What the Cool Girls are Wearing This Fall

And believe it or not, that’s one of the main reasons I started this style blog for women over 50 four and a half years ago. Because I needed something to hold me accountable to getting dressed for my day and getting out there. I needed to keep pushing myself forward so I didn’t let myself slump into a comfort zone that would swallow me up and cause me to disappear. I needed to keep learning, keep investing, keep growing and keep trying.

And somewhere along the way I realized that I wasn’t the only one. You sweet ladies showed up and I had someone to sit with. You became the girlfriends at that lunchroom table, saving me a seat and a carton of white milk to swap for my corn. And then I didn’t feel so dorky or alone or clumsy. Especially as our number grew (to over 15,000 email subscribers and almost 115,000 YouTube subscribers!!!) and I realized we are the cool girls! Because it’s cool to be humble, to know your strengths and your weaknesses, to admire the accomplishments of others and cheer each other on. It’s cool to walk into a room and forget about yourself and focus on other people and on putting them at ease. And it’s cool to finally realize that you may not be perfect, but you are perfectly created and perfectly placed into your little corner of the world to do what you can to make a difference. Yeah, that’s pretty cool.

What the Cool Girls are Wearing This Fall
similar pants // similar sneakers (more economical option) // belt // tank // denim jacket (plus sizes) // necklace // similar earrings // similar shoulder bag (more economical option) // similar bangle

I repeat, you’re one of the coolest girls I know. And if you want to rock sneakers with wide leg dress trousers and a denim jacket, you go girl. And if you don’t want to wear that…that’s cool, too. Because whatever you wear today…that’s what the cool girls are wearing this fall.

Hahaha! I crack myself up. Thanks for reading my ramblings, sweet friend. No, I don’t have a fever. Have a great day!

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

Spread the love

Blessed for My Day

I guess I’m feeling a little nostalgic and a little sentimental today. So indulge me while I go on to thank you from the bottom of my heart for showing up here. I don’t always respond to your comments. Over the years the number of emails and comments I receive here and on Instagram and on YouTube have grown and I feel a little overwhelmed by them most days. But I absolutely read and sigh and chuckle and tear up and share them with my husband and my daughter and my mom. Your comments and emails keep me going. They bless me. You bless me.

I wanted you to know this today because I’m doubling down and recommitting to showing up here each day for you. Yes, I know I’ve been doing that. But I want you to know that I’ve been praying about this platform and I want to make sure that I keep on using it to the glory of God and your good. I want this blessing to truly bless you. And I’m going to start including a blessing at the end of each video, too. Why? Because every woman needs a little encouragement, a word of hope, a reminder of the truth. And I am committed to offering you that here and there. Thank you for showing up, sweet friend. 

I do not cease to give thanks for you, remembering you in my prayers. ~ Ephesians 1:16

xoxo, Kay
Join the Conversation

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

49 thoughts on “What the Cool Girls are Wearing This Fall

  1. Thank you, Kay. This was such a good post. Thank you for your honesty and encouragement! God bless you!

  2. Awww…thanks Kay! This is just what I needed to hear today. You are such a blessing to those who stop by your blog. Glad you two are feeling better!

  3. Kay,
    I too at 5’8” felt like the jolly green giant at school. Towering above the boys. I have homecoming pictures of me bending my knees in order to be shorter , thinking no one could tell but the dress was sheer and highlighted by the sun it was obvious. So embarrassing at the time.
    Thank you for all your thoughts, blessings, and fashion advice. I think I’m finally getting it and I’m 63!

  4. This is the best fashion post I’ve ever read. Thank you. You know you’re cool when the cool girl acknowledges you! 🙂

  5. Thanks Kay, for your heartfelt words today. Thank you for showing up, being real and encouraging your readers to do so too. God bless you.

  6. Oh, Kay you just have no idea how much I needed to read this today. I woke up today feeling down in the dumps for no reason. I was on vacation last week so I’m calling it the post vacation slump. Anyway, you reminded me just how much I have accomplished in my life even though I sometimes feel I should have done more by 52. Thank you for sharing your heart.

  7. I loved this post and just love you, Kay, for your transparency and humor. I actually WAS a cool girl back in the day, so the fall from grace has been much harder as I grow old. Your posts keep me trying and today, I’m just going to think of myself as a cool girl again and go out there and be my best self!

  8. Honesty, authenticity, loving-kindness…. Thank you for your inspiring blog today. It is just what I needed to hear.

  9. Your best post yet! I didn’t get asked to my junior prom either ☹️. And my philosophy is you have to get dressed every day anyway, why not try your best? Also, not much I can do about my face and body getting older but I can still dress nicely! And modern! It’s nice to find a blogger who share that attitude!

  10. This is one of the coolest blogs I have read.
    You are cool and sweet and a God fearing woman. You make me laugh. I too was that awkward middle school high school girl. Except I wasn’t tie was short and skinny and flat chested. I’m still short, but now I’ve put on a few pounds and sometimes I think too much.
    God bless you. Loved your BFTD! So fitting and true

  11. I’ve never commented on your blog, but after reading this I felt compelled. Thank you for sharing this beautiful post. You are so right. We are all ‘cool’ girls.

  12. I actually felt very emotional reading this and it brought tears to my eyes. Thank you for such a well written blog.

  13. Thank you Kay for your transparency! I think we often feel like we are the only uncool girl and everyone else has it so together. You can sit at my table any day cause I think you’re amazing and we all appreciate your encouragement so much!

  14. You were so “spot on” today. Even those cool girls (who we thought were cool) had frumpy days. If they say otherwise, I must raise an eyebrow. Your post today was honest, vulnerable, clever, fun, and oh soooo relatable. Have a cool day on this pretty chilly, cool day! Lol

  15. Kay, you are always a delight! Being who we truly are is always cool! Too bad we didn’t know that when we were younger. I very much enjoyed this post and am so glad you are over the Covid. I also had it a couple of weeks ago so I shared your pain. Thanks for showing up here every day. Missed you while you were sick but glad you took the time to heal. Blessings on you girlfriend! Keep up the encouraging work!

  16. Great post today! Thank you for being so “real” and sharing the vulnerable parts of yourself. I LOVE that you played the French Horn in high school. I am a professional French Horn player in Mobile and have had quite a long career. If you are ever in the area and would like symphony tickets, please let me know.

  17. Thank you, Kay, for being YOU, the cool woman of God you are! I appreciate your encouragement today as I await my mammogram. Your authentic self blesses me! I love your realistic fashion helps, also!! Rockin’ 60 with your great example!!

  18. Your message today really touched me. There are definitely times that I feel invisible, feel I don’t matter. Your encouragement is a blessing, and so appreciated!!
    Thank you, Kay!

  19. Oh, Kay, you really covered a lot of very human challenges today – how we seek to fit in yet still be valued individuals, and not be tied or judged by our intelligence level, physical or social strata realities, income or possessions. If you have ideas on how to help our granddaughters (pre-teens, teens, young adults) weather or rise above the self-doubt to become confident young women, please pass them along. I guess we always want to make our kids’/grandkids’ paths smoother, though I know we each have to walk our own path. Reminders from you that God loves me and all of us mean so much. God is truly working through you. <3

  20. It’s hard to imagine that a woman as stunning as you didn’t have a special chair at the cool table in the high school lunchroom. Life sure takes us down different paths and I believe you now hold that very special chair. Being short myself with bad posture due to a bum knee and now sore hip from still trying to treadmill, fashion is a challenge. My son in Michigan just took us on a boat ride on Lake Charlevoix past some adorable hobbitt houses and as beautiful as they were, I was glad I don’t hobble into one of those everyday, LOL. Thanks to your encouragement to “dress cool”, I still get many compliments on my fashion and I can’t tell you enough what that does for my self-esteem! Hugs to you, cool girl, for all that you do in saving all of us a seat at the “cool table”❤

  21. What a beautiful post, Kay! THANK YOU! Your blog is definitely one of the many blessings in my life. I’m glad that you are able to attend the Bible study today.

  22. My term these days is “hot girl” similar to “cool girl.” At my age, I call myself a hot girl when my outfit and look makes me feel good. My daughter laughs, but I catch her using the term too. Lol
    From one hot girl to another, have a great day:)

  23. Great article, Kay. I’m sure 99% of us could relate. And yes, we are now the cool women!

    And so happy you are feeling better.

  24. One of the nicest things that you do for women, is the opportunity to post pictures of themselves on your Facebook page. I always click like because I want to continue to encourage them. I think that it takes a lot of courage on their part to do so. But where else can you get unbiased approval and constructive criticism.

  25. Thank you Kay for your post! I am glad you are feeling better. I don’t normally leave comments but I always look forward to receiving your post. It’s good to get to a point in life where we are comfortable with who God has made us to be. After all, we are “cool” in His sight.
    I would like to also say Thank you for your modest choice in clothes. I believe that we can still dress modest and look nice. As an over 60 woman, I don’t want to look old but I don’t want to look like I’m in my 20’s either. Your post has been quite helpful. Keep up the good work – you are appreciated!

  26. Hi Kay, I loved this!
    We are all trying to accept our aging bodies and be visible, and I’m so very thankful to have this day to plan and enjoy.
    I thank you for your humour, humility and style. 🙏💕

  27. I enjoyed this post a lot. When I think back to high school, I thought life revolved around high school. Then someone told me real life starts after high school. That me me very happy. I now know that was correct. Thanks for sharing this, but I still think you’re cool😎 Have a great day!

  28. Dear Kay, I don’t often comment but I do read your emails every day. I’m very glad that you are much better!
    Today’s post about the “cool” girls was such a winner. I’m sure most everyone has had similar feelings at some point in their lives. Bless you for sharing yours. I love your passion of helping us show up for our day…thank you!

  29. Thank you for this beautiful post today, Kay! I look forward to reading your blog everyday! You are an inspiration and a blessing to me – I’m sure all of your readers will agree. And I must say, you have definitely helped me to dress like one of the cool girls in recent years 😃 Have a beautiful blessed day!

  30. Really enjoyed your blog post today, Kay. Very well put and right on the money. Appreciated reading it and you for posting it!

  31. You know, God made each of us wonderfully and unique and special — so why in the world do we allow ourselves to become caught in the insecurity trap?!?! I’ve spent SO much time stuck in my insecurities and awkwardness, and still do on occasion, despite that fact that my age is waaaaay closer to Medicare than middle school. I agree that it IS easier to lose the bad attitude now than then, that we don’t have to live our lives in middle school hoping for a seat at the table, because now we know that WE can offer a seat to someone else who might be riding in on the awkward bus. Thanks, Kay!! You bring a ray of sunshine each day. And I’m so glad that you are feeling so much better!

  32. Thank you so much for this post and making us all feel we are one of the “cool” girls. Love your posts ….keep doing what you are doing! Appreciate you sharing your your faith and not being ashamed to do so.

  33. I’m so blessed to have found you!! I am a 56 year old high school teacher; so I see all sorts of style!! Trying to stay current can be a challenge but it keeps me young. Some of my best friends are other teachers under 40 who always say they love my style! Keep encouraging us! Love your heart Kay ❤️

  34. In December of 2021 I went back to work in financial services after a ten year absence. I had worked at Lowe’s where wardrobe needed to be more practical. That coupled with my advanced age ( I’m turning 60 this year), had me seeking advice about an appropriate wardrobe. That’s how I found Dressed for My Day. The advice and teaching have been invaluable. Ok, so now I have all the clothes I NEED! Now I have challenged my self to utilize my pieces in different ways! Creating different outfits, again, great advice Kay! However, I come back to your blog for posts like today! The inspiration you bring to these kinds of real conversations is the true strength of your blog (in my opinion). Inner beauty, spiritual growth, and acceptance of ourselves and the challenges of life at this stage is something we all have in common! I truly appreciate the work you have put into your business! I wish you health and joy in all that you do!

  35. I loved every word in this post, but you cracked me up with “No, I don’t have a fever.” Thank you so much, Kay! I am glad you are feeling better and I am SO glad that you are doing what you do. I have learned so much from following you, and I especially love Blessed for My Day.
    I am working to make a difference in my little corner of the world. After retirement and then Covid shutdowns, I am still trying to figure out what that looks like. But God is showing me, as I keep my eyes on Him.

  36. Thank you, Kay. You help us all to be cool! I so appreciate your transparency and fashion sense and your love of God. Have a good day!

  37. You are a blessing to me, Kay. I read your “Blessed for my day” each day and it brings a smile to my face and joy to my heart. I often find you remind me of something just when I need it most! I’m so glad you’re committed to continue. I’d miss you if you weren’t in my life.

  38. Kay, you are a blessing, a delight, and I’m so glad God is using you in this way to reach women, to be an encouragement!

  39. Kay, thank you so much! I am 66 and have been “collecting sisters” all my life! You are a dear! I love this post, and the genuine loving spirit with which you share of yourself. I love getting dressed for my day. Now that I’m retired, it looks different but I still want to show up and allow the light of God’s love to shine through me to everyone I meet.
    God bless your day!
    Twila King Wilkins, a sister in the Buckeye State 🙂

  40. Your message today truly blessed me! Thank you so much for sharing your heart and helping us all to feel “cool” and worthy. We are all so unique but, at the same time, have so much in common. This “aging thing” is sometimes hard. It’s nice to know we are not alone in our struggle.
    I want to save this to remind myself to just be my own “cool” and love and cherish this gift of life God has given me.
    And…YOU are oh so cool girl!!!

  41. Hello wonderful Kay! Thank you for your words of encouragement and kindness. You certainly reflect Our Heavenly Father. I am late to reply, but better late than never! Glad you’re better! You and all the sweet girlfriends are in my prayers.