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

What to Wear on a Messy Day This Fall

September 28, 2023
Sponsored by Kohl's and Collective Voice

Just because it’s a messy day outside, doesn’t mean we have to look a mess. But I do think that getting dressed on a messy day goes a little easier if we’ve put a little thought into our rainy day outfits ahead of time. So today I’m sharing a couple of ideas from Kohl’s for what to wear on a messy day this fall.

Jeans with Tee and Hoodie
trouser jeans // long sleeve tee // Nike sneakers // earrings // zip-up hoodie // shoulder bag

Now these are not fancy outfits. These are the kinds of things I wear on messy days when I just have to get out. I want to feel warm and cozy, and honestly I’d rather stay inside. But necessity gets me out in the weather. The temptation is to slum it. But I believe we can still dress cozy, comfy and casual, but also look pulled together and even a little stylish.

Jeans and a Tee with Sneakers

So I chose to wear trending full leg trouser jeans from Lee. They’re comfortable, but still look stylish and fun. Mine are in the shade blurred darks, so a faded black wash. They also come in a few shades of blue denim. They fit true to size; I’m wearing a size 10. For this dreary day, I topped them with a black and ivory striped long sleeve tee, but this soft, comfortable tee also comes in many other fun colors. It’s also true to size.

zip-up hoodie

If rain gear isn’t necessary, I’d just slip on an easy-going zip-up hoodie. I’m wearing a medium for a true to size fit in this ivory hoodie. It’s also available in black, grey and blue.

Travelon anti-theft classic mini shoulder bag
Travelon anti-theft classic mini shoulder bag

It’s a good day for a water-resistant bag, so I chose to strap my Travelon anti-theft classic mini shoulder bag across my shoulder. This is the same bag several of my travel companions used on the streets of London recently, and they all said they really enjoyed it. It has lots of anti-theft features, but it also has the pockets you desire for ease of use.

Nike Sneakers
Nike Sneakers

I’m seeing these Nike sneakers everywhere. They have a fun little detail on the back of the shoe. And I find that they fit comfortably true to size. You can get them in several other fun patterns and color options, too.

Dreary Day Outfit

I think this outfit looks very suitable for getting out on a messy day, but it’s still contemporary and stylish. But if there’s a chance of rain, I’m going to carry along an umbrella and even wear a raincoat.

Rain Coat

This Fleet Street short trench raincoat features a removable hood, a water-resistant shell and a warm removable inner liner. I think it will make the perfect raincoat to take on my Alaskan cruise next summer. But meanwhile it works perfectly for rainy days right here. I’m wearing a size medium very comfortably.


I also like that you can snap and zip the front of the coat closed. And it has some nice zip pockets, too. This is not a lightweight coat, but when you remove the liner it does lighten up quite a bit. I think it’s perfect for fall and early spring.

Holding Raincoat

My particular umbrella is no longer available, but I think this similar Totes travel umbrella with cats and dogs is adorable. Being prepared for a rainy day with an umbrella and a water-resistant coat and handbag is smart. And while I’m all for giving ourselves a little grace on rainy days (and Mondays!), I do feel so much better when I still get dressed for my day stylishly and thoughtfully.

Rainy Day Outfit
Fleet Street short trench raincoat // trouser jeans // long sleeve tee // Nike sneakers // earrings // Totes travel umbrella

I found everything I needed for these messy day outfits at Kohl’s. And I earned Kohl’s cash with my purchases. Not only can you earn Kohl’s Cash with your purchases today, but you’ll also get 20% off your order with code FAMILYSAVE. And don’t forget about Kohl’s free store pickup option, too.

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!

Don’t Miss a Post:

If you like what you’re seeing here at Dressed for My Day, I invite you to subscribe to my email list. You can receive an email each time I post (about 6 times weekly) or just on Saturdays. You choose! But you’ll also receive the password to open up all the subscriber freebies I offer.

Would you like to subscribe to Dressed for My Day?

Spread the love

Blessed for My Day

This week we’re looking at the story of Jacob and Esau’s reunion in Genesis 33 to learn a few truths about forgiveness. Tuesday we learned from Esau’s gracious attitude toward his conniving brother Jacob that he must have done the work of forgiveness first with God so that he could walk it out later with his brother. Forgiveness is an act of grace that best comes from having experienced the grace of God firsthand. Today I’m struck by Esau’s response to Jacob’s attempt to earn his forgiveness through gifts.

When Jacob tries to earn Esau’s favor with cattle and sheep, Esau replies, “I have plenty, my brother; let what you have be your own.” I think that perhaps one of the reasons Esau was able to forgive his brother for stealing his birthright and blessing is because somewhere along the road he learned that God had indeed provided everything he needed and more. He didn’t really lack anything. If someone has taken something from you or withheld something you feel you deserved, you may feel cheated. And if we focus on what we lost or never received, we’ll always struggle to forgive. On the other hand, if we’ll focus on the sufficiency and generosity of God, we’ll soon feel much more generous and gracious toward our offender.

And he said, “What do you mean by all this company which I have met?” And he said, “To find favor in the sight of my lord.” But Esau said, “I have plenty, my brother; let what you have be your own.”  ~ Genesis 33:8-9

xoxo, Kay
Join the Conversation

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

15 thoughts on “What to Wear on a Messy Day This Fall

  1. Thank you for these messy days dressing ideas. My husband and I are also going on an Alaska cruise next summer! How great if it was the same cruise and I was able to meet and say hello to you. We will be on HAL’s Koningsdam sailing on July 13. Can’t wait!

  2. Hi Kay,
    I have appreciated you encouraging us to try new trends out.
    A couple weeks ago I found a pair of dark wash flair (or maybe boot-cut) jeans at a second-time-around type of shop and tried them. I really liked them. This past week I found a dark wash wide-leg jean (with dark stitching) and will try this style out. So, under $30 I get to “taste” these wider leg jeans! One thing that attracts me to them is the space in the lower leg/shin area because I wear an AFO brace that takes up room in a lot of straight leg pants.
    In the late 60’s and early 70’s I had a couple wide leg pants that were common on college campuses. I just am a little shy to get back to using them. But I think I’ll enjoy wearing these again.
    I hope you have an enjoyable trip to TX. Thank you for all you do for us older gals. God bless. J

  3. Perfect Kay ! I love your ‘Messy Weather’ Outfits Simple , Stylish and Cozy . In the UK we get a lot of that Messy Weather 😂🌧💦☔️So this Post is just right 👌🏻. Im also loving your ‘Forgiveness’ BFMDs ❤️. Enjoy your Convention and have Fun . You and James have a lovely time visiting his Family , safe journey and hope your foot is settling down a bit . Loved your video yesterday about Elevated Basics so many good tips from you Thank you Xx

  4. Love these looks! I do hope you can let us know more about your Alaskan cruise trip because my husband and i were talking about one for our anniversary in June. It’s been a bucket list item. I’m just not sure where to start? Do you mind if I ask what cruise line you’re going with? I need to start looking into this. Thank you!

    1. I cruise a lot. Holland America line is geared towards the older crowd. They don’t have wild parties, the casino is small, they have interesting lectures, classes…I recommend them over Carnival. Disney is even better, but more children and more expensive.
      I wonder if Kay is reticent about naming her cruise line-she might have creepy people following her and she may not feel comfortable sharing that information.

      1. We cruise a lot too, Karin. I would never recommend Disney. I would definitely choose Carnival over Disney.

        Hahah, I assure you I’m not a “creepy” person. We’re booking this trip in August. Thanks for the laugh!

        1. I didn’t mean YOU were a creepy person-I meant there might be some. I had some creepy things happen to me so I’m always on the alert. I forget that other people are not:)

          My experience with Carnival was not great, but I know some people like it.

  5. These outfits are very “me”‘ always appreciate whe you feature items from Kohls. Ad the St John’s bay jeans the other day. These are what real women wear. I think every women I know has at least one pair of Jeans in that brand. With a wide range of sizes and styles, they are my go to for jeans.

  6. Kay,
    I did not know where to ask you a question.,so here it is.

    Could you give me the name of some influencers that are tall. I am 5’11 and 69 y/o
    Maybe you will find some at your conference.

  7. Thanks for mentioning the hoodie is ivory, it looks white on my phone. I’m looking for a white hoodie with a zipper preferably fleece lined and have not been to find one anywhere!

    BFYD- I heard a saying that vengeance is like drinking poison thinking it will hurt your enemy. Not forgiving someone hurts yourself. One caution is that someone who has been deeply wounded-rape, sexual and physical abuse…should receive empathy and help before being told they should forgive. A lot of hurt to the wounded can happen if we don’t walk with them through their trama first. Forgiveness will lead them to freedom and should be address-but first they need empathy, love and a hug:)

  8. Kay, I may not always have time for your well-thought out blogs, but I always have time for Blessed for My Day. I love this sharing of the word of God and the uplifting of me every day I read it.

  9. I really didn”t like the wide leg jeans . I’m short they would make me look frumpy. I did not like them the first time around I am sorry they brought them back.