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Styling a Pleated Midi Skirt for Winter

February 10, 2022
the Winter Classic Style Series 2nd annual

Today I’m killing two birds with one stone. Well actually no birds will even be harmed in this blog post, much less killed. You know how much I love birds! However, today’s post is a part of two different style mini series. First, I’d definitely consider today’s pleated midi skirt outfit a winter classic. And it is indeed all styled from items in my closet. But this outfit is also one of four that I’ll be styling this year with this classic pleated midi skirt.

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Styling a Pleated Midi Skirt for Winter
floral pleated midi skirt // crewneck pullover sweater // similar leather jacket (more economical faux leather jacket) // suede slouch boots // shoulder bag // knotted bolo necklace // bangle // earrings // fleece tights // camisole

About the Pleated Midi Skirt

One of my “style resolutions” for 2022 is to wear more skirts and dresses, even on “regular days.” Plus, several of my readers have been asking for more outfit posts with skirts. I tend to wear a good many dresses in the course of a year, but I’ve never felt quite as comfortable in skirts.

Until now.

Pleated Midi Skirt

This flowy 100% polyester floral pleated midi skirt is so comfortable and fun to wear. In fact, you won’t have to wait until spring to see me style it again. I wore this skirt working from home Tuesday, so it will make an appearance in Friday’s How I Really Dressed for My Day post. It feels oh so soft on the skin and has such a lovely drape. I do think that is one of the keys to choosing one of these trending skirts. Look for one with a good drape, a little weight, so it doesn’t “poof out” on you too much.

I had been quite hesitant to even try this style of skirt, fearing it would add visual weight. But since I ordered this floral pleated midi skirt and fell in love with it, I challenged myself to style it four different ways over the course of the year, one way for each season.

Styling the Pleated Midi Skirt for Winter

Pleated Midi Skirt and Cashmere Sweater

The day we shot these photos it was a brisk 12 degrees outside. But since there was no wind, I actually felt just fine in my skirt outfit (well, for long enough to shoot the pictures!). I’ve definitely layered on the warmth here. So first, let’s talk about what you can’t see. Under my winter skirt outfit I’m wearing these fleece tights and this camisole. Staying warm while looking chic is all about wearing thin but substantial layers close to the skin.

Cashmere Sweater

I’ve got a few ideas for how I might style this skirt for spring and summer. But for our frigid winter it seemed to make the most sense to top the pleated midi skirt with a cashmere sweater. I could have worn one with a different neck or fabric composition, of course. But this camel colored crewneck pullover sweater gave me the look I was hoping for…a little understated and very simple to balance all the flounce and frill and florals going on below.

I also kept my jewelry classic and pared back. I wanted it to be impactful enough to be seen, but nothing fussy. I love this knotted bolo necklace for wearing with plain front sweaters. And my bangle and earrings are pieces I wear almost daily.

Leather Blazer with Pleated Midi Skirt

Of course, I also simplified my jewelry because I knew I’d be wearing my leather blazer over my outfits. Those bold gold buttons are plenty of jewelry in and of themselves! That said, a single strand of pearls would have looked nice here, too. In fact, they would have balanced out all the splashes of gold quite nicely.

Leather Blazer with Pleated Midi Skirt

My black Veronica Beard Gaya leather blazer was an investment purchase I made in 2020 with the help of some Nordy notes I’d earned. I’m so glad I have it in my closet and reach for it even more than I thought I would. But you could certainly achieve the same look with a faux leather blazer, or even one of a different fabrication. I just felt like the skirt and sweater combo needed a jacket that would lend a little more structure and shape.

Black Suede Boots
floral pleated midi skirt // crewneck pullover sweater // similar leather jacket (more economical faux leather jacket) // suede slouch boots // shoulder bag // knotted bolo necklace // bangle // earrings // fleece tights // camisole

My black suede boots seemed like the obvious footwear for this winter edition of my pleated midi skirt. I purchased these at the same time I bought the skirt, I believe. But they quickly sold out. Interestingly, they have one pair in stock as I write this…in my size. Ha! These are GREAT boots and fit true to size. You just slip them on. I have wide calves, but they go on just fine. Ann Taylor has a few other boot selections here.

Styling a Pleated Midi Skirt for Winter
floral pleated midi skirt // crewneck pullover sweater // similar leather jacket (more economical faux leather jacket) // suede slouch boots // shoulder bag // knotted bolo necklace // bangle // earrings // fleece tights // camisole

I felt perfectly comfortable and pretty in this pleated midi skirt outfit. In fact, I wore this that evening to meet friends from church for a burger. We took these photos in Lebanon, by the way. I know some of my Ohio readers like to know where I’m shooting. That was the first time I’d been there, and I can’t wait to go back so I can browse more and eat at The Golden Lamb. Someone gave us a gift card for Christmas!

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Blessed for My Day

My son Daniel always loved playing on teams when he was growing up. I believe he enjoyed the comradery of his teammates more than he did the sports or competitions they shared. I like working with teams, too. But even sweeter than teamwork is the love and fellowship and common goals shared by a church family. There’s just nothing like a church family.

Look, I’ve been hurt by church families. I mean, I’ve taken some major blows from churches. But that doesn’t keep me from valuing and enjoying the fellowship and love of the group of people I do life and worship with now. God intends for us to grow within the context of a church family, a group of fellow disciples. I hope you have a church home where you get that kind of encouragement and support and love. That is God’s best for you. If you do, be grateful. If you don’t, why not begin this weekend looking for a church family to call your own?

We ought always to give thanks to God for you, brothers, as is right, because your faith is growing abundantly, and the love of every one of you for one another is increasing. ~ 2 Thessalonians 1:3

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xoxo, Kay
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19 thoughts on “Styling a Pleated Midi Skirt for Winter

  1. Very nice outfit! Love the way you can wear that skirt as you’re a bit taller than 5 ft 3 me. Not sure I could pull this off, Kay. But you look great.
    As great as the leather blazer is, you could also include the camel blazer over the camel sweater? That might also look very nice?
    Thanks for all the hard work to bring us this wonderful blog and a daily blessing.

  2. OMG, The Golden Lamb! Such great memories. We had friends who lived near Lebanon and we’d drive from Lexington, KY to their house for the weekend for many years the week before Christmas and stay with them and have dinner at the Golden Lamb. So glad its still there. That was back in the early 80’s!!!!! Love the look you are sharing. My kind of style. Thanks.

  3. Hi Kay……I had only been there one time but my parents ate there a lot on special occasions. I did buy a Lamb ornament to remember my visit and the memories my parents made when they ate there.

    Love the skirt and maybe there is a less expensive one like it out there…..will keep my eye out. Also the gold tone buttons on your jacket really pop with the skirt camel color. Such a cute look. Super cute boots too!


  4. I know what you mean about wearing dresses more than skirts. I think skirts might look more casual sometimes than dresses, but this long one, the way you are wearing it is so cute on you, Me being 5’3″ I usually do not wear long skirts except with boots. Interesting how you did black with the skirt. It looks like there is blue in it? I might have worn a navy blazer or camel and brown accessories. Is there black in the skirt too? Hard to tell on line sometimes. Anyway looks nice.

    1. Hi Sherry. There’s lots of black in the skirt. It does have a little bit of blue, but when I tried blue with it, it looked off. I still may try something blue in one of the other stylings. This skirt is very versatile. So many options.

  5. I enjoyed BFMD. I too have been hurt by church families and I am not in the ministry and then I mourn the loss of the family. That must be terrible for you and your husband. Take care. Love your skirt outfit today. I would like to wear more dresses or skirts but I rarely go out except for the market. I feel very isolated. I really enjoy your blog and it helps me get through the day.

    1. Hi Rory. I’m so glad you find community and joy here. Thanks so much for being a faithful reader and showing up here in the comments so frequently. I don’t always get to reply to all the comments. But I read every one of them and I always enjoy seeing yours. ?

  6. Good Morning from Canada-I love this blog,started following for the fashion but `Blessed for My Day` is now my favourite part-I also love my church family and we have been so blessed through this pandemic-I pray for your congregation and the steps you are taking to Glorify our Lord and Saviour-enjoy the day! Grace

  7. Looks very cute today. My question is about your handbag. Does it have enough structure to stay upright, say like on the car seat when driving. I am thinking about the Taramisu color; thinking I have black covered .

    Enjoy your day

    1. Hi Barbara. I’m out and about with that bag right now and it is sitting upright on a seat next to me. It’s a great bag. Very versatile. I’ve had it a few years now and I actually have it in two other colors too.

  8. As beautiful as that skirt looks on you, that Veronica Beard blazer is such a darn show stopper it’s hard to notice anything else. I’m gnawing my right arm for that right now, lol.
    Another great blog, Kay!

  9. Kay,
    The v- neck camel sweater in your video looks like it has a finished edge on the vee or maybe you wore a shirt under it. I like little details on clothes so I’m curious.
    The Golden Lamb looks like a great place to stay a night or two at. It’s a bit far from me unless I visit my brother in Navarre and have time for both stops and continue home. I like to discover new places.
    Sorry to hear about your experiences with the church. You may be held to a higher standard because of your role there and preconceived notions about leaders of the church. The offenders are missing the point. We are human. And most of all ….judgments should be left to the Lord!

  10. That outfit looks great on you. Thank you for styling skirts; looking forward to more! I tried a pleated skirt recently but I always feel they make me look too big even though this one seemed to hang well. Maybe it would just take getting used to or maybe I need another opinion lol. I choose skirts over dresses because I just can’t usually find a dress that works for me. I’m normally a medium in tops and large in skirts with smaller bust so it makes it hard.
    Thanks again – love that you’re giving us style options with skirts.

  11. I lived in skirts for years and with boots was a favorite ways to style them in the winter. I’m looking forward to your spring version of this skirt. A black Tee with a French quote and sneakers. Or a pretty white blouse with nude pumps. No fashion blog for me, HaHa.

  12. Dear Kay, I am so sorry to hear you have been hurt by church family. I know my husband and I have as well. To quote a pastor at a church we were a part of for years, if you are looking for a perfect church please go elsewhere, we are a church full of imperfect people. We always remember that people are imperfect but God is perfect. Look to him and trust in him.
    I’m praying for you and your husband.
    Love the outfit and the different styles.