This Cool Pleated Pant Trend Looks Amazing on Women Over 40… But It’s Tricky!

Pleated Pant Trend

This is one of those trends I was super excited to try – I’m talking about the pleated pant trend! Have you seen those street-style photos of women looking so cool and chic in their slouchy trousers with their sneakers, blazers, tanks, and bra tops? They look SO amazing, right? So I wanted to find a way for us 40+ women to embrace the trend too. But let me tell you, it wasn’t easy…at first. While pleated pants can certainly give off an “effortless” vibe, styling them was actually a bit of a challenge! BUT, I did find ways to rock them after some trial and error. Keep scrolling for ways to wear this hot trend without looking frumpy. For more details on the trend, the challenges, and to see some of these outfits in motion, make sure you watch this video too.

 If you are as excited about fashion trends as much as I am, be sure to read this post where we highlight our favorite spring/summer trends…and how to make them wearable!

pleated trousers women

But First, The Challenges

Let’s take a minute to talk about the issues you might be facing that make this trend seem a bit daunting…

  • You might be petite like was impossible to find any petite-length pleated trousers when I first tried this trend! The ones I ordered were way too long and had to be tailored. But now that the trend has been going strong for a while, there are more brands offering cropped or petite options. I’m sharing a petite pair of pleated pants that I recently found and love below…
  • What if you have a tummy? Since pleated trousers add bulk around the midsection, it may seem counterintuitive to try this trend. Especially for older women who might have some extra weight in the midsection (thanks, menopause). But it actually can be flattering if you can find the right pair of trousers.
  • Overall, pleated trousers add volume so unless you are super thin and tall, how do you pull off this look without looking swallowed in the pants?

Keep scrolling for the best ways to combat each of these challenges!


How to Wear the Pleated Pant Trend

Look #1) T-Shirt & Sneakers

For a casual and cool look, you can wear pleated trousers with a simple tee and sneakers. In this look, I’m wearing a ribbed white tee with eyelet detailed flutter sleeves (only $49!) and a pair of Favorite Daughter pleated pants. These are the best pleated pants I’ve found. And it’s mostly because they come in petite length (29.5” inseam). The pleating is also not too voluminous, which helps with the tummy issue if that’s a concern for you. I styled them with a pair of platform sneakers that makes the length perfect with a little bit of puddling at the bottom that’s on-trend.

If you aren’t comfortable tucking in your tee completely, try the half tuck. So you can get some forgiveness on either side and some waist definition. You could also add a waist belt like I did. Now, if you have a tummy, and tucking in isn’t flattering for you, just find a shorter or cropped tee that barely touches the top of the waistband of the pants. But, not an oversized or boxy tee. You need something that is body-skimming to give you some shape.

Pleated Pant Trend women over 40

Look #2) Button-Down Shirt

The next pleated pant outfit I recently wore on a trip to Vienna. I wanted to look a little more polished and pulled together so I styled my pleated pants with a chic white button-down shirt. This is a look you could wear to the office, but you have to be careful with the kind of button-down you choose, This one is more body-skimming versus oversized, which helps control the proportions and balance of the outfit. I styled it with the same sneakers from the last look but you could swap those with heels for the office or flats for running errands or a lunch. What I love about these pleated pants is that you can pretty easily mix and match the tops, accessories, and shoes to build the perfect outfit for your lifestyle or plans.

Whitw Tank and Pleated Pants

Look #3) White Tank

One super easy way to sport the pleated pant trend is with a ribbed or simple white cotton tank. In this look, I’m wearing a white tank by Free People with pleated trousers by L’Academie. First I want to talk about these trousers…they are one of the best options I found during my original search because the pleating isn’t too over the top. With a lot of the trendy pleated trousers out there, the pleating is WAY too big, which make the tummy look bigger. With a softer pleat, you can avoid that issue.

But, with oversized pieces like these trousers, getting the proportion and balance right is key! The tucked-in tank helps define my waist and creates some balance with the baggy silhouette of the pants. I did have these pants hemmed so they’d work with both sneakers and a low-heeled shoe. If you are under 5’7″, you’ll probably need to do the same. To keep this look casual and really wearable, I paired the pants with Golden Goose sneakers but you could also throw on a pair of slides. Very simple and very chic!

casual baggy pants outfit

cropped blazer outfit

Look #4) Cropped Blazer

If you’re looking for a bit more coverage than a tank or tee can provide, a cropped blazer is the perfect third layer for pleated pants. It does a beautiful job of nipping in the waist and giving the illusion of a defined waist even if there isn’t one! It also adds polish and sophistication. The one I’m wearing is unfortunately sold out, but I linked a few similar options below. You could also wear a cropped moto jacket or denim jacket to achieve this same look.

baggy pants over 40Pleated Pant Trend for women

Look #5) Body-Skimming Blouse & Heels

I wanted to share an office-appropriate option or a dressier option for pleated pants. In this look, I’m wearing a Team Busbee favorite, the Wayf lace top. I believe the team purchase count is somewhere around 10 blouses…and we don’t have 10 people on our team! See what I mean when I say it’s a favorite? Not only is it lovely and high-quality, but it’s also very affordable. I paired it with darker, camel-colored pleated trousers and gorgeous Malone Souliers pumps to dress it up. Heels in the same tone as the pants will help elongate your legs which is another trick to making slouchy or oversized pants, look more slimming. These exact pants are sold out, but these similar trousers also come in camel along with 5 other options including black.

slouchy trousers trend

slouchy trousers trend women over 40

Look #6) Ruched Top

Here’s another idea for the office. This time I paired the camel pants with a black top with some very strategic ruching. I love the flattering details on this Frame tee (yep, it’s a tee) with the puff shoulder, fitted sleeve, ruching, and v-neck. The ruching is helpful with hiding a tummy. And the cropped length is perfect for these pleated pants because it hits right at the waistband…no tucking required! This look is polished but doesn’t feel fussy at all. The exact top is sold out. But I linked some similar tops that will help you achieve the same look. I’m wearing a pair of old Jimmy Choo two-toned pumps that worked perfectly with this color combo but you could also wear neutral heels, camel, or all-black. The pointed toe helps elongate the leg too so that’s something to consider when choosing your footwear.

baggy trousers womens fashionPleated Pant Trend for women


I wanted to share a bonus look – 2 ways!  On the left, I’m wearing a streamlined white Cinq a Sept blazer with the lighter L’Academie trousers. This is a cool girl look…very casual with the sneakers. On the right, I’m wearing an oversized, boyfriend blazer that adds quite a bit more volume. I wasn’t super comfortable with this look at first. But the fitted tank underneath creates waist definition. The heeled sandal adds some height, and now…I’m actually really loving it! I dig it but, full disclosure, it even intimidates me! The key to pulling off either a streamlined or boyfriend blazer with your pleated trousers (and not looking like you are drowning in fabric) is not closing the blazer. Leave it unbuttoned so you can see the waistband of the pants.

What do you think? Do you love to hear that you can ditch your skinny jeans for baggier pants or are you skipping this trend? Please share in the comments! To get blog posts delivered right to your inbox along with other incredible style resources, be sure to sign-up for the newsletter here. AND…if you liked this post, we’d love for you to share it with a friend using the buttons below.
Thanks so much for reading!

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Join the Conversation

5 thoughts on “This Cool Pleated Pant Trend Looks Amazing on Women Over 40… But It’s Tricky!

  1. Hi,
    I enjoy your tips! I’m 68 (size 6, 5’7″) and I’ve already worn almost all of these styles shown for beige pleated. I even have a cropped camel jacket that is very similar, and a white blazer! I purchased beige linen very baggy, pleated pants in Paris in May (made by Marc O’Polo). Of course, I’m larger than you, but the look works. Now that fall is coming, I tried them today with a silk navy sweater tucked in, black Coach gold belt, and Cole Haan tri-color slingback mule loafers. I added a structured high-hip navy pique blazer. It works!

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