Mother and daughter in style

Spanning 40 Years: Beautiful Styling Of Pleated Midi Skirts

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There are so many options styling pleated midi skirts, and I have not just one, not two, but four options that span 40 years with three different body shapes.

Quote of the day: “Fortune does favor the bold, and you’ll never know what you’re capable of if you don’t try.” Sheryl Sandberg

As I’ve explained in the past, there are many advantages to wearing a flowy skirt instead of pants. While so many women have given up wearing skirts and dresses for some reason, I hope I might be able to twist your arm to embrace them.
I always say it’s nice to have variety in our closets.

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Tips on Styling Pleated Midi Skirts

Gone are the days when styling pleated midi skirts was for a fancy, dress-up affair only. Now you can wear them for every day and even pair them with sneakers.

Sometimes, the best way to get ideas about styling pleated midi skirts is by seeing how the models are wearing them on retail sites.

Insider tip: “Copying” the younger kids with how they style items from our youth, is a great way to modernize the look. Otherwise, if you wear it the way you always wore it in the past, it can give off a frumpy vibe.

While I dismiss the worry about adding visual weight to your body by styling pleated midi skirts at the end of this article, it is helpful to follow these tricks.

  • Tuck in or wear a cropped top: As much as possible, you want your shirt to end at the waistband of the skirt. That is NOT to say you can’t wear a longer top with your pleated skirts, but it will be more challenging.
  • Length: There should be no rules, but everyone has some preferences. Remember, skirts are easy to alter by shortening, or sometimes you can roll the waistband up to make it shorter temporarily.
  • Change it up: Try some interesting color combinations or different materials for styling your pleated midi skirt. You don’t have to stick with a cotton skirt.

There have been other examples of styling midi skirts if you would like to see more examples.

Summer Styling for Pleated Midi Skirts

Pleated midi skirts are extremely versatile since they can easily be worn for both warm and cold weather.

Charlotte and I will show 2 summer options, and then Cathie and Charlotte will showcase 2 cooler-temperature outfits.

Insider tip: Volumous skirts are super heat-friendly no matter what material they are. Because they don’t hug your body, they allow for airflow and keep you much cooler.
Plus they are bathroom friendly. They pull up instead of pooling on the floor.

Black Pleated Midi Skirt and Summer Top

Charlotte is living proof that you can wear a black pleated midi skirt and look summery.

She paired her skirt with this colorful collared top and then tied it at the waist.

Insider tip: Isn’t this blouse beautiful? You wouldn’t know until you look at the label, but it’s a pajama top. Who cares? It’s the perfect reason not to categorize our clothing.

Then instead of wearing matching black shoes (as she did in the winter styling pleated midi skirt outfit below), she chose floral flats.
This lightens the look fabulously.

And the cherry on top is the watermelon slice purse. A touch of whimsey is good for keeping you young at heart.

Pairing Brown and Turquoise

My pleated midi skirt is not just any ordinary skirt. It’s not only tulle but asymmetrical as well as layered.
It’s also a larger size than my normal, but I knew I could make it work.

Insider tip: These cardigan clips have push-open clasps on each side under the metal portion. So while it looks like I’m wearing a belt, this clip is pulling the elastic tighter in the front of my skirt.

Even though the skirt is brown, which isn’t a color you see as much in the summer, I wore it with a turquoise sleeveless top, floral shoes, and fun accessories.

Even my purse which was given to me by a friend when her mother passed, was decorated with a turquoise skinny scarf along the handle. This is the video that inspired the scarf hack.

Floral shoes with pleated midi skirts

Colder Weather Styling for Pleated Midi Skirts

Both Cathie and Charlotte are showing you how they can transition styling pleated midi skirts for either a casual or a fancy occasion.
In all reality, both Cathie and Charlotte styled the same outfit. Dark pleated skirt with a white top and then a jacket as a third layering piece. Yet the details make it all look so different.

Black pleated skirt outfits for midlife women
Skirt: Notations ~~Jacket: Time & Tru-thrifted ~~ Top: no label~~ Shoes: Adidas -thrifted ~~ Purse: Rebecca Minkoff-thrifted

Casual Version: Black Pleated Skirt Outfits

You’ve met Cathie on the blog before when she joined us wearing navy. If you think the three of us are good thrifting shoppers, you will love Cathie. She has introduced me to many of my thrifting haunts and is an amazing deal shopper.

Notice too that Cathie’s black pleated skirt is longer than Charlotte’s skirt. Yet the length of a skirt does not necessarily make it fancy or casual. It’s all about the other details that give off that kind of vibe.

Cathie went with a plain, white tee and pink denim jacket. She is wearing a delicate gold necklace, yet her crossbody fuschia purse acts as an accessory.

And then for her footwear, she is wearing her white sneakers. Sneakers are not just reserved for working out, leggings, or joggers. It’s a modern approach to comfy footwear that women can wear with anything, including their black pleated skirt outfits.

Red blazer and black pleated skirt outfits
Skirt: Love Fire -thrifted~~Jacket: Chaus ~~ Top: Mom made it ~~ Shoes: Caparros~~ Purse: Rue 21-thrifted

Fancy Version: Black Pleated Skirt Outfits

My mom is still in the way of thinking that a skirt is for dress-up. I understand it’s hard to change our thinking when we have done something for so long.

Reality Check: Stagnation doesn’t look good on anyone. For example, we want all kinds of changes in how women are treated in the workplace. Possibly a 70-year-old man would think that women shouldn’t be in the workplace because that’s how he had grown up. We want change when it’s convenient for us, right?
Yet change is constant and that includes our style and fashion.

Yet there’s nothing wrong with wearing the black pleated skirt outfits for fancy events, and Charlotte has that idea down pat.

Charlotte wore a red blazer as part of her styling a pleated midi skirt. It’s a bold color that can be worn with any other color or neutral.
Red is such a wonderful color to incorporate in the winter months since it’s so appropriate for the Christmas holidays as well as Valentine’s Day.

Accessories to Work with Red and Black

My mom’s birthday is in January, so she has a lot of garnet jewelry that she has gifted to herself. Even though the garnets tend to be a darker red than a bright red, they work wonderfully paired together.

Notice how my mom not only wore one garnet necklace but she layered 2 of them with this outfit. She then just hung a scarf around her neck to tie in the dark skirt and red and white of the top half.

Insider tip: Too many times we stress over HOW to tie our scarf, when in fact, it’s the beautiful fabric of the scarf that is the focus. Sometimes all you need is to hang it around your neck for it to be a wonderful focus. By doing this, you also keep the front open to be able to see the necklace party.

I love that my mom brought her boho-style purse to pair with this look. In fact, the design of the purse mirrors the scarf pattern. Yet you’d never call the scarf boho. This is why it’s always better to stop categorizing our clothing!!

Longer blazer for older women

Do Pleats Add Visual Weight?

Who cares? Don’t worry that a pleated skirt could make you look bigger. That whole idea that being smaller is better has been brainwashed into our society WAY too much. Instead, it’s a fun style that moves and is easy for anyone to wear.

Sure, we should strive to be healthy. Yet loving our bodies as they are is the most freeing thing for our minds. Whether that means your body has some scars, dimples, or any such sort of “extra” on it (I refuse to call them imperfections anymore).

Personally, growing up with pale skin in the 80s no less, was always a struggle. I would try to tan, burn, and work SO hard on not being pale. I look back on those days and think what a waste of time and energy. I have pale skin. Does it bother you? If so, then you can make fun of me. But I embrace it and I only hope to inspire others to love themselves.

Want to hear the best story from Reader’s Digest about this subject? It’s in my post all about my journey embracing my pale legs.

Styling pleated midi skirts for older women

Photo credit: Rob Filogomo

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