What to wear with a pleated skirt—3 easy styling ideas to try today

The staple midi skirt is back. Unsure what to wear with a pleated skirt this time around? We've got three failsafe outfit ideas...

Two models showing what to wear with a pleated skirt. They style them with knitwear and statement shoes
Left: Hush | Right: Mango
(Image credit: Hush | Mango)

Before we get into what to wear with a pleated skirt, let's all take a moment to appreciate this humble midi style. It's having a moment once again simply because it's universally flattering. 

Fashion trends come and go, but items that can be worn on rotation across all seasons—like the best cashmere sweaters or the best winter coats—have staying power. The pleated midi skirt is one of those pieces. And often seen on the likes of Victoria Beckham, Meghan Markle, and Holly Willoughby, we're not surprised it's become a mainstay in so many capsule wardrobes

Sitting above the ankle and below the calf, it skims legs and thighs and allows you to see a flash of your favorite shoes. The pleated non-clingy cut is also great for skimming figures—with just the right amount of floaty and fitted. The one rule when it comes to how to wear a pleated skirt though is you must wear them on the waist. This isn't a style to have sitting on your hips—the cut won't hang correctly, and that can add width. 

Despite its popularity, it's not always obvious how to style this skirt, but our fashion team has three failsafe pleated skirt outfit ideas for you to try.

What to wear with a pleated skirt—3 outfit ideas

So, how do you wear a pleated skirt? For daytime or after-dark, they make a great alternative to a Christmas party dress. We're here to show you some simple style tricks for this season and beyond. 

1. Pleated skirt + blazer

Style influencer Karina (@styleidealist (opens in new tab)) demonstrates an around-the-clock way to style the must-have midi. Pairing a printed iteration with wardrobe basics (a white t-shirt and blazer) is a way to keep the look polished. Incorporating a tailored jacket that skims over the hips is a great way to make the floaty skirt more structured and it stops it from feeling like a lot of fabric around your middle. 

What you need...

A styling tip...

Karina wears hers with sandals but for fall and winter, switch to a knee-high boot. You can also layer your warmest leggings underneath once the temperatures drop and no one will even know. 

2. Pleated skirt + fine knit

Opting for a fine knit jumper means you're not adding any bulk to the skirt and this can easily be tucked in to define your waist. You can of course wear this as an evening look with heels like the presenter Holly Willoughby, or it will look just as good with laid-back sneakers or heeled ankle boots. For the cherry on the cake, add a coat in a similar shade for a very Meghan Markle take on the skirt. 

What you need...

  • A fine knit
  • Nude heels for evening or laid by sneakers for day
  • A tailored coat or jacket 

A post shared by Holly Willoughby (@hollywilloughby) (opens in new tab)

A photo posted by on

A styling tip...

As a fan of the pleated midi skirt for years, UK tv presenter Holly Willoughby (who always manages to make high street pieces sell-out, fast) gives a lesson in how to wear it. The simple way to style this type of skirt without having to think too much about it is by picking a block colour for your entire outfit. If you're not a fan of winter white then any colour will work, but the styling trick is to go matchy-matchy with top-to-toe tonal. 

3. Pleated skirt + chunky boots

Modest fashion influencer Rebekah (@iamnkirote (opens in new tab)) is wearing all of this season's key trends, at once—pleated skirt, Breton striped sweater, and chunky Chelsea boots (our fave shoe trend this year). The stomper boots have gained kudos among the most stylish of women over the past few years and they're the perfect way to keep the pleated skirt casual. 

What you need...

A post shared by Rebekah Nkirote (@iamnkirote) (opens in new tab)

A photo posted by on

A styling tip...

Pick a sweater with a thick thread style. It off-sets the floaty fabric of the skirt and makes a cool clash that totally works as a winter look. 

Where to shop pleated midi skirts at a glance

Ready to start styling but need a wardrobe upgrade on your pleated skirt first? We recommend the ranges at these stores, in particular Hush and Mango, where the skirts featured above are from:

  • ASOS (opens in new tab)—petite, regular, and plus pleated skirts from $34 / £25
  • Cos (opens in new tab)—minimalist, everyday pleated skirts from $95 / £69
  • Hush (opens in new tab)—printed and metallic styles from $95 / £69
  • Mango (opens in new tab)—affordable pleated skirts from $28 / £19.99
  • Ted Baker (opens in new tab)—fun, printed pleated skirts from $206 / £150

Harriet Davey is a freelance fashion editor, writing and styling for titles including Vogue, Stylist, Grazia, Who What Wear, and woman&home. With over 10 years of experience in the industry, Harriet has a love for shopping but also a newfound interest in trying to be more sustainable. With a love for Scandi brands and an eye for key designer pieces to mix in with high street hero buys, Harriet specialises in shopping stories and buying guides that’ll make you feel excited about updating your wardrobe.