An influencer wearing a short pleated skirt.

A Different Pleated Skirt Outfit for Every Day of the Week

There’s no doubt about it: Pleated skirts are having a moment. And they’re so cozy-cute we want to wear them every single day of the week. Of course, styling such a bold item can be challenging—especially if you don’t want to go full school girl every time you slip on a pleated mini. (We certainly don’t hate the school girl aesthetic—we just love variety too much to sport it 7 days in a row.) So how do we create midsize and plus-size pleated skirt outfits that are genuinely different? By turning to those who already love wearing the trend, of course.

As we’ve discovered, styling pleated skirts is an art. Influencers, bloggers, and fashion-lovers make it look easy, though. These folks know exactly what to pair with their pleated minis and tennis skirts to turn them into *chef’s kiss* looks—and we’re taking notes (quite literally).

Think: tennis skirts worn with button-downs and sweater vests, along with pleated mini skirts paired with oversized sweatshirts and thigh-high boots. Sunday through Friday (with an extra look thrown in—because you can never have too many), these trendy folks have you covered from head to toe. Frankly, we couldn’t be more obsessed with the midsize and plus-size pleated skirt outfits they’ve come up with so far. (And this is only the beginning.)

1. The Sweater Vest & Button Down Combo

why she loves it

“I have been obsessed with the pleated skirt trend. First off, I love a good skirt moment and wearing a mini-length can be so freeing! I spent so much of my life trying to hide my thighs and legs, so it’s become more than a trend to me. It’s never too late to show off those gams—don’t let some cellulite, lumps and bumps stop you!”

how she styles it

“My favorite way to style a pleated skirt has been to keep it preppy—pair it with an oversized sweatshirt or an Oxford shirt and sweater vest. Keep it comfy and don’t forget the sneakers!”


2. The Ruched Crop Top & Cardi Look

why she loves it

“I have loved bringing back the pleated skirt. I wore a uniform skirt all through schooling and it provides a really flattering shape. Drawing attention to your waist!”

how she styles it

“I usually style it with a tight top that is a fun pop of color or with a cute sweater vest.”


3. The Blazer & Boots ‘Fit

why she loves it

“I love how versatile pleated skirts are because you can pretty much wear them with any outfit at any time of the year. Whether it’s a tennis skirt for a cute spring look or a plaid skirt for autumn, there’s never a reason not to wear one!”

how she styles it

“I love to style pleated skirts with a roll neck and knee high boots! It just gives me serious Clueless/Legally Blonde vibes.”


4. The Graphic Sweatshirt & Thigh-Highs Look

why she loves it

“I love that pleated skirts are so versatile. They can be worn in any season; in the summer with a light top or crop top and in the winter with tights and warm top. You can dress them up or down. They come in a variety of lengths, materials, and styles. They are just an overall closet staple.”

how she styles it

“I love styling them with an oversized sweatshirt, button down blouse, or turtleneck.”


5. The Cropped Sweater Vest & Sneakers Ensemble

why she loves it

“I just think they’re a bit of fun and I feel really confident in them.”

how she styles it

“My favorite way to style is to dress them down with a pair of trainers and either a T-shirt or a sweater vest.”


6. The Fuzzy Sweater Set

why we love this look

Staying cozy is our prerogative in any season—and a coordinating sweater set is the perfect way to wear a short pleated skirt no matter the weather. If it’s chilly, slip on the cardigan. Or if you get a little too toasty, ditch the cardi and keep on the matching knit tank. You can’t go wrong here.


7. The Puff-Sleeve Blouse & Heels Combo

why she loves it

“I definitely love how simple the trend is, yet looks so chic and feminine. It is also one of those clothing pieces that in my opinion looks flattering in so many different body types and is such a fun way to spice up a basic skirt. Also, it reminds me of being back in my very religious catholic school! It sounds cheesy, but I loved the girly uniform, haha.”

how she styles it

“For a more casual look, my favorite way to style it would be with a form-flattering bodysuit, and to dress it up a bit, definitely a puff-sleeve blouse and some fun heels.”


8. The Button-Down & Slip-Ons Outfit

why we love this look

Pairing a plaid pleated skirt with a simple white button-down and white slip-on sneakers is a classic look that can’t be beat. Sometimes, simplicity is the way to go—and allows the pleated skirt to serve as the star of the ensemble.