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Pleated Midi Skirt Styled 2 Ways for Fall

September 12, 2023

Do you have fun with fashion? While I do think it’s smart to take into account things like proportions, body shape, contrast in intensity and optimal coloring, I also think it’s important to keep fashion fun. Or at least, I think it’s good to have fun with it occasionally. Why am I starting today’s blog post on a pleated midi skirt styled two ways for fall this way? Hmm. You’ll see. 😉

Styling a Pleated Midi Skirt 2 Ways for Fall

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A Pleated Midi Skirt Styled for Elegance

For this first look I definitely took a more traditional approach to styling this beautiful deep chocolate brown pleated midi skirt for fall. This pull-on skirt features an elasticized waistband that folds into the skirt, leaving the waistband smooth and seamless. It runs true to size; I’m wearing a medium comfortably. The skirt is also available in black, camel, navy, ivory and blue. Oh, and you can get it in a print, too.

Pleated Midi Skirt for Fall
suede block heel pumps, (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only)

A couple of years ago, I styled a pleated midi skirt from Ann Taylor for each season of the year. Maybe I’ll try to do that with this one, too. They’re so versatile and I find them quite flattering. For this first look I envisioned wearing the skirt to church or a special event. So I topped it with a cropped cashmere sweater and completed the look with my suede block heel pumps, also in chocolate brown. (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only)

shrunken cashmere sweater // chain necklace
shrunken cashmere sweater

Actually J.Crew calls it a shrunken cashmere sweater, and it does run on the smaller side, although I’m wearing my usual size medium. I tried the large and it was roomier, but lost its cropped effect. Don’t let the terms cropped or shrunken fool you or keep you away. A lot of brands are sharing cropped length sweaters and tops these days because they work so well with the fuller silhouettes of jeans as well as high waisted anything. This one is 19.5 inches in length and covers the waistband of my skirt completely with no risk of baring my midriff as I move about.

pleated midi skirt // shrunken sweater // suede pumps // necklace // earrings (similar) // bracelet // similar clutch
pleated midi skirt // shrunken sweater // suede block heel pumps, (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only) // necklace // earrings (similar) // bracelet // similar clutch

While I generally like to keep the contrast in intensity low in my outfits, I think this one works well for me all the same. the heather stone colored cashmere sweater seems to be a good neutral for me, so I like it around my face. I’ve completed the look with simple but impactful gold jewelry and carried my brown suede clutch from last year (same bag updated for this year).

clutch (updated for this year)
clutch (updated for this year)

Proportion-wise, this shrunken sweater paired with a brown pleated midi skirt and brown suede block heel pumps definitely produces those desirable 2/3 to 1/3 proportions. I think this look is easy on the eyes and a little elevated, but definitely still comfortable and not at all fussy.

Styling a Pleated Midi Skirt 2 Ways for Fall
pleated midi skirt // shrunken sweater // suede block heel pumps, (Use code SARAHFLINT_CCLAURAKAY1 for 15% off at Sarah Flint, new customers only) // necklace // earrings (similar) // bracelet // similar clutch

I would style my pleated midi skirt like this for church, dinner out for a special occasion or another nice event. And I think this style formula would work really nicely with a different colored sweater, too, such as rose, peach, red or even lavender. But let’s move on to another way to style this skirt. Buckle your seat belts!

A Pleated Midi Skirt Styled for Fun

Next I styled my pleated midi skirt…for fun! Honestly, I fell in love with these croc-embossed cutout loafers first. And I was just itching to style them with this skirt!

Pleated Midi Skirt Styled for Fun

I’m sure my croc-embossed cutout loafers are not everyone’s cup of tea. But I absolutely love them. Not only are they very on trend and youthful, but they’re extremely comfortable, too. I do think it’s important to style these lugsole cutout loafers with modern pieces or they can look quite frumpy. But I like to think I was at least on the right tract with my pleated midi skirt, simple crewneck tee and trending cashmere vest.

vest // t-shirt
vest // t-shirt // bracelet // earrings (similar)

I added a little more joy to my fun outfit with a sparkly bracelet and simple earrings (similar) .

Pleated Midi Skirt Styled for Fun

I’ll also wear these Italian leather cutout loafers with jeans and pants, but I’m all for experimenting a little with fashion. So I thought it would be fun to wear them with a skirt here. We’ll never be fashion forward unless we are willing to take a few risks.

shoulder bag
shoulder bag // bracelet

I kept my handbag choice simple and a little subdued. I’ve really loved carrying my Kate Spade Hudson convertible shoulder bag.

Pleated Midi Skirt Styled for Fun

I don’t allow myself to posts any outfits I wouldn’t be 100% comfortable wearing in “real life.” So I’m pleased to tell you that I’m actually wearing this outfit today. I have a nail appointment and plan to make a few stops afterwards. We’ll see how it goes!

Pleated Midi Skirt Styled for Fun

If nothing else, you have to admit I shared two very different ways to style a pleated midi skirt for fall. Ha! I have a feeling I’ll be sharing this pretty chocolate brown skirt again, too.

Pleated Midi Skirt Styled for Fun

Thanks so much for stopping in today. I hope you have a blessed and beautiful day!

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Blessed for My Day

Are you between a rock and a hard place? Maybe you could use a little good news. If you’re going to be up against something hard to handle, the best place to be is on the Rock. God wants to be your rock, your firm foundation, in good times and bad. He can provide you with the sureness of foot that you’ll need to stand up under the pressures of this life. At the same time, He provides a soft place to fall when it’s all just too much to deal with.

Instead of trying to calculate your next move or fortify for the next blow, turn your attention to the God of your salvation. Call out to Him. Run to Him. He can provide you the love you will need to get through this hard place with courage and strength. Lean into Him and He will not let your slip. Trust Him and He will carry you through.

I will lift up my eyes to the mountains; From where shall my help come? My help comes from the Lord, Who made heaven and earth. ~ Psalm 121:1-2

xoxo, Kay
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20 thoughts on “Pleated Midi Skirt Styled 2 Ways for Fall

  1. Until this morning I didn’t think a pleated skirt was my style. But you have changed that. I could happily wear that second look. Thanks for making us stretch. Thank you for the comfortable shoes too, I am battling planter fasciitis from over use and these certainly look better than sneakers. I never thought I would get tired of sneakers.

  2. Your skirt with the cashmere sweater and heels was perfect on you. Looked so lovely. I will be interested in seeing the croc loafers styled with pants/jeans for a fun look. When you said they could end up looking frumpy, that word came to my mind looking at them with the skirt. A very good DFMD . Have a good day. Thanks for your visual addition to yesterday’s post

  3. I like both outfits, but I *love* the shoes! I have a pair in a similar style and it’s always a bummer to put them away when the sloshy, icy winter arrives. Great post today to get us to stretch a little.

  4. I like the chocolate brown skirt.but on me a 5’3 frame it would be too long. That’s ok can’t buy everything those sometimes I think I try. Lol I like the first outfit the best. No offense, The second outfit looks too dumpy or maybe its the shoes. We can’t like everything we are all different when it comes to style. Maybe because I am short I know the outfit would swallow me up. Better for a tall person. Again no ofense. Have a blessed day.

  5. You look lovely in that skirt, Kay. I am a petite hourglass, and it’s just not a look I can pull off. I always admire them, though. Now, the second shoes you showed—I think I am in love lol. What JCrew calls a loafer, I call a T-strap Maryjane. I have loved those since I was a little girl and am so excited to see they and regular Maryjanes are back! I hope you don’t get flack for having a little fun with fashion. I hope you will let us know if you got any reaction when you are out and about today! Thank you for leading us to stay current and try new things! And your BFMD is something I really needed.

  6. Love, love the first outfit of the pleated shirt and cashmere sweater. Ditto for your hair. But did not like the second one at all, especially not the shoes. Sorry, sweet lady.

  7. Oh.My.Goodness. I’m in love with those croc shoes. What an adorable outfit. Thank you for this “out of our comfort” zone outfit. I think it’s super fun, super youthful and it looks super comfy. I bet you get loads of complements on this outfit today!

  8. I’m 83 now so I often wonder whether to even try some of the outfits such as the cute casual one today. Would your mom wear it? As we age we get shorter and thicker waisted– messes with proportions. Just the midi skirt itself feels risky. On the other hand it’s possible I could go for the croc loafers (Mary Janes).

    1. Hi Evelyn, First of all let me commend you for at least having an open mind about this style. I think it’s so important that we stay open to possiblities…at least if we really want to be a little fashionable. I don’t know for sure if my mom would wear these shoes or outfit or not. But I really think it’s more about your personal style aesthetic, maybe your personality and, of course, your body shape and proportions. So I just try things. I don’t always show the things that don’t work out for me, but trust me, there are plenty. But I do try things. And I encourage you to try things that intrigue you. When I do try something new, I give it all the chances I possibly can. I tried these shoes and skirt so many different ways, some of them even a little “wilder” than this. Ha! And I liked some and didn’t like others. But I put my makeup on, did my hair and really tried to make things work. I think that is key – putting yourself completely together, not just putting something on and calling it a try. Make sense?

  9. I like the first outfit, but I think the second one is too masculine for me, especially the shoes. I don’t know why. I’m petite, under 5 feet, and I agree with the comments that a full pleated skirt would swallow us up. However, when I worked, I had several knee-length (slightly above so the knee shows) pleated skirts where the pleats started at the hip, so the waist to the hip was just like any other skirt. I have to say, wearing that type of pleated skirt worked for my frame. It might work for other petites, too. I usually wore a blouse, but the sweater is great too.

  10. I am loving all of the chocolate brown we’re seeing lately. The pleated skirt is so pretty. I like it with the sweater. I enjoy wearing midi skirts, pleated and straight, with boots or something chunky like your lug sole loafers. You look so stylish in your outfit. I’m sure you will get lots of compliments at the nail salon!

  11. I think the first outfit is very classy and I would wear it much as you described: to church, a luncheon, special event, etc. The second outfit is ok I guess, but personally, I find those shoes very unflattering and clunky. And I’ve never quite understood the short sleeve tee shirt with a sweater vest. If it’s chilly enough for a sweater vest, why would you wear a short sleeve shirt? Why not wear an actual sweater? Or if it’s warm enough for a tee shirt, why wear a vest? It looks pretty in a photo, but doesn’t seem practical to me.

  12. I love the coordination of colors in the first outfit. In my opinion, the red and brown combination in the second outfit is too jarring. I think your pink vest would have worked better.
    Not a fan of the shoes with a skirt. I think they would look better with pants.
    Kay, thank you for all that you do for
    women to enhance us mentally, physically, and spiritually! I look forward to your blog posts and Instagram messages. Keep up the great work!

  13. Love this skirt on you! The first outfit is so elegant. I especially love the red and chocolate together for the second outfit. And I do believe the shoes are growing on me! It’s all about perception for me. Remove the mental images of the “older” ladies in the past wearing them and insert a new perspective. And as you said, it’s all about your attitude when you’re wearing them. Thanks for stretching us all here, but by bit! Have a blessed day.

  14. Kay-
    You are beautiful inside and out. I love that you have chosen to guide women in faith while pairing with fashion! Your blog posts are so good for my soul. Thank you!

    Yes, I love the chocolate pleated skirt! But more than that I love how you give permission to be who we are in terms of personal style! This reminded me of the ‘box of chocolates’.saying. I tend to enjoy each chocolate in the box no matter it’s filling lol, and the same goes for the creativity you showed in styling these in two different ways!

    Today I discovered a Talbots A-line Tweed skirt that reminds me of confetti. I’m going to wear it to a baby shower for one of my daughters to thank God for his great blessings and to celebrate their spontaneous identical twin boys to be born near Christmastime! Thought I’d share my ‘interpretation’ of the skirt with you and anyone else who is celebrating! If you look through the tweed skirts I believe you will easily see what I did. It’s a ‘joyful’ skirt in my opinion.

    Blessings as you await your new grandchild! Prayers!

  15. You look so pretty in both outfits. I LOVE the Mary Jane shoes! I like the juxtaposition of the feminine skirt with the t-strap shoes. Thank you for the BFMD, too.

  16. Sorry I’m late in responding but I love this skirt and I love both looks on you with those too cute shoes. I am 5’3″ and I have worn pleated skirts and pants successfully. Classic style for sure and you wear it well, Kay!