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Styling a Denim Skirt 2 Ways for Early Fall

September 5, 2023

It’s just the day after Labor Day, so I know real fall temperatures are still a distant dream for many of us. Then again, the afternoon we shot these photos the temperature was a sweet 68 degrees Fahrenheit. So there’s no time like the present to start thinking about what we’ll wear for those early fall days, especially when the temps are a little up and down. To that end today I’m styling a denim skirt two ways for early fall.

A Denim Skirt Outfit for Early Fall

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I’ve mentioned in recent posts that I’ll be sharing more outfits with repeat items in future posts. I think it’s important that I share multiple ways to wear the garments I’m adding to my own closet. Plus, denim skirts are so very hot this year, they’re deserving of our attention. I did style the J.Crew denim skirt in this previous post with a t-shirt and cashmere sweater. Be sure to check that post out if you missed it. That skirt is sold out right now, but I’ve seen them restock it before, so maybe they will again.

denim skirt
belt // denim skirt (also here and another option and another) // booties

Today I’m sharing a denim skirt (also here) by Rails and it features the deconstruction blue jeans look. The midi-length denim skirts are the ones really trending right now, and I’ve noticed that they all sell out super fast. I bought this one the minute I saw it for that reason, and later purchased the one from J.Crew. I have a size 29 in the J.Crew skirt, but I wear a size 30 in this one comfortably.

white button-up shirt
white button-up shirt (and here) // belt // denim skirt (also here and another option and another) // bracelet (similar option in gold) // necklace // similar earrings // tote (no longer in this color)

For the first look I styled the denim skirt with a simple, oversized white button-up shirt (and here) from Citizens of Humanity. As much as I love my Frank & Eileen shirts, this Citizens of Humanity shirt is my favorite for one big reason: it features buttons up the sleeve with which you can button the cuff to the sleeve for a secured “roll-up.” Ingenious! It’s very comfortable and on trend, too, of course. And this is such an easy way to style your favorite denim skirt.

A Denim Skirt Outfit for Early Fall
white button-up shirt (and here) // belt // denim skirt (also here and another option and another) // booties // bracelet (similar option in gold) // necklace // similar earrings // tote (no longer in this color) // sunglasses

I completed that look with my light sand colored suede booties that I purchased in the Nordstrom Anniversary Sale. They’ll be great with jeans, but these light colored booties are perfect for dresses and skirts, too. They run true to size.

Next up I styled the denim skirt with a simple graphic tee and sneakers. You’re probably going to get sick of me saying this, but I saw hundreds of women in England wearing dresses and skirts with their sneakers and they looked amazing.

denim skirt for early fall
similar graphic tee // belt // denim skirt (also here and another option and another) // sneakers // earrings // tote // bracelet

My light sand colored On sneakers are great with this look. And I love that I can just slip them on and off. My t-shirt is sold out, but any graphic tee in your collection would work just as nicely here.

similar graphic tee // belt // denim skirt (also here and another option and another) // sneakers // earrings // tote // bracelet

You may have noticed that I did add my cognac colored belt to both outfits. Remember, thinner belts are coming back in style this year. And I’m a fan. If you need a jacket with your denim skirt, reach for a moto jacket or utility jacket.

utility jacket
utility jacket (similar option and another option) // similar graphic tee // belt // denim skirt (also here and another option and another) // earrings // bracelet

My utility jacket is low in inventory and size options, but it’s a good one. But here I found you a similar option and another option. The good thing about wearing an army or olive green utility jacket is that you don’t need to feel compelled to match it to your top or anything else in your outfit. Nothing here exactly matches, but it all “goes together” really nicely, creating a decidedly casual vibe.

sneakers // tote

I completed that outfit with a tote I purchased last spring from M.Gemi. I haven’t used it a lot so far, but I think I’ll pull it out and carry it more this fall because I’m really crushing on this color for accessories.

Denim Skirt with Tee and Utility Jacket
utility jacket (similar option and another option) // similar graphic tee // belt // denim skirt (also here and another option and another) // sneakers // earrings // tote // bracelet

So those are two fun ways to style your midi length denim skirt for the early fall. If you’d like even more style inspiration for denim skirts, let me know in the comments. Thanks so much for dropping in today!

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Blessed for My Day

The longer I walk with the Lord the more I am learning that God always has my best interest at heart. And because He is good, I can trust Him to always lead me in the best path and never to lead me astray. When I lean into Him, I can dwell in safety and I find rest for my soul…even if things appear uncertain around me. But when I try to figure out next steps on my own, I revert to feelings of insecurity and fear.

Let’s choose to trust the Lord today. Let’s remember that He paid a high price for us and He will not lead us astray. In big decisions and small moments, let’s turn to Him for guidance and trust that He knows what is best. And let’s take a deep breath, let it out slowly and rest in His provision. 

This is what the Lord says, He who is your Redeemer, the Holy One of Israel: “I am the Lord your God, who teaches you to benefit, Who leads you in the way you should go.” ~ Isaiah 48:17

xoxo, Kay
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18 thoughts on “Styling a Denim Skirt 2 Ways for Early Fall

  1. I was wondering, since we can now wear denim jackets with denim trousers, if we can also wear denim jackets with the same type skirt. And still be seen as fashionable! ;0)

    1. Hi Pat, I think you absolutely could. I personally am still not really comfortable wearing denim jackets with denim jeans or skirts. But it’s certainly on trend. Good question!

  2. I love your denim skirt options! I found a great one at Kohl’s and a lovely moss green denim skirt at Talbots! I can’t wait to wear a cropped chunky sweater with them when the weather cools. I love the look with a tall boot as well. Happy birthday to your daughter! I love that you saved that special mug!!

  3. How sweet that you kept the coffee cup gifted to you when Abigail was born and drink your coffee from it on her birthday. I too think back about the day my children were born. Sweet memories. Nice BFMD.
    Love the skirt. I have a longer dark denim skirt in my closet from about 3 years ago. Is dark denim in skirts in this year also? think I will pull that out when it cools down here. is suppose to start Cooling down here soon. I don’t wear denim or Jens in the summer. Too hot. Have a blessed day.

    1. Hi Kay! I love your looks for transitioning to fall with the denim skirt. Please style it in a winter look in a future post! It is so sweet that you celebrate your daughter’s birthday with your special cup. I have a beautiful mug that I received from my infertility doctor after the birth of my precious son 25 years ago. It sits on the dresser in my bedroom holding trinkets. I think I will follow your lead and drink my coffee in it on his upcoming birthday! Thanks!

  4. Hi Kay you look Fabulous in your denim skirt outfit options , and I love that you have shown us the skirt with your beige bootees , I love that look , but have wondered if us older ladies could carry it off , but looking at you Yaaaaaaay we can !👏🏻👌♥️. I love how you said you kept your special coffee mug from when Abigail was born and drink your coffee from it on her birthday 💞Aren’t these memories of our little ones ( now grown) just so magic ? and lift our hearts so beautifully . I saw this quote today and thought I would share it .
    ‘The most treasured gifts are the wonderful moments we create with the people we love .They. become priceless memories decorating our lives.’

    Have a beautiful day Kay ♥️

  5. You are totally rockin this jean skirt, Kay! And your makeup looks great👍. Love the mug in honor of Abigail 🎉, and I am taking much comfort today in your BFMD. Enjoy a most blessed day!

  6. I don’t have a denim skirt but I’ll be looking out for one; I thought your pictures looked great. Meanwhile I’m in denim shorts. Yes, here in SE England the weather has gone mad and we are up to 86F. It’s going to be hotter tomorrow! I thought your packing for London was brilliant – we have to cater for sun and rain and wear layers. No sign of rain here for the next week though. On Friday I am going into London for lunch with old friends and yes, it will be a dress and (trainers) sneakers. I am not looking forward to the Underground! Special thanks for BFMD – I needed that today.

  7. Cute outfits, Kay! I am looking forward to imitating them! Would you mind sharing some more information about the belt? Specifically, could you please tell me:
    1. The size belt you are wearing – is it an XS/S or M/L?
    2. Your waist measurement?
    3. How long the belt is from the center of the buckle to its other end when it unbuckled and laid flat?
    4. How many inches are “left over” after you buckle it?
    I appreciate your help as the comments in the J.Crew website seem to give conflicting information, probably because ladies are using it for pants with different rises. I think my measurements are similar to yours, so your answers would be greatly appreciated!
    Also, I copied an outfit from your blog last week and received many compliments on it! I wore a black short-sleeved tee with cognac chinos, accessorized with a black belt and black loafers. Such a simple but chic outfit! Thank you!

    1. Hi Kim. I’m wearing a medium/large with lots of belt left over after buckling. My waist is about 30 inches. I think the belts probably run true to size for a large and for a small, and I you need an X small or Medium you’re just going to have belt left over.

  8. I wear jeans nonstop but am a little unsure about a denim skirt. I love the look but lack the occasion to wear one, I think. Both looks are really nice, and LL Bean has several jackets, including a cropped utility jacket that would be perfect with a denim skirt. BTW, I really like your new haircut. The bangs give you a youthful and flirty look (in a good way).

  9. Hi Kay, these outfits are so cute! I love them both. I especially love the thinner belt. Can you help with sizing? I can’t find a size guide on their web site. I tend to run between a small and medium, and am never sure which way to go with a belt. Thanks for such a great blog!

    1. Hi Ruth, if you run between a small and medium you’d probably do well with the xs/s. I’m wearing the medium/large and have lots of belt left over.

  10. There are many cheaper versions of white shirts. I think Kay gets a lot of free things. Also, if you watch for them, there are good sales at the end of season.

  11. I don’t look good in that length, but you inspired me to try these ideas with my short denim skirt even though it may not be on trend. They are so cute!

    I do think of the day my children were born on their birthday. They are such darling dears.

  12. The last time I wore my denim midi skirt I styled it just like you with a white shirt. I wore it with sandals. When the weather is cooler I will wear it with booties. My skirt looks very similar to yours. I bought it 2 years ago for about $5 at Banana Republic factory. It was on sale and I had a good coupon. One of my best purchases ever. Even after it’s no longer trending I intend to keep it because it’s really a classic.