The Pretty Skirt Trend That’s Made Stylish New Yorkers Forget All About Jeans and Leggings

Every fashion capital has its unique charm, but there’s just something about New York style that always gets me.
With style icons like Chloë Sevigny and The Olsens amongst their own, no one masters effortlessly cool quite like the New Yorkers. So, when a trend starts gaining traction on the city’s streets, you can bet I’m paying attention. And this week, I spotted a skirt style that I knew instantly was going to take off.
A voluminous retort to the pencil skirt trend that's proliferated for the past few years, this swishy silhouette brings movement and drama, with generous folds of fabric creating a full, circular shape.
Whilst this skirt naturally pairs well with slim-fitting shirts for a sleek finish, I find myself drawn to a more-is-more approach—think square-shaped jackets, oversized knits and plenty of texture.
A key transitional piece as we move towards the warmer months, the generous fabric provides coverage while still feeling light, and it’s roomy enough to layer up with tights—or even leggings—when there’s still a chill in the air. Then, as temperatures rise, go bare-legged and pair a circle skirt with strappy sandals or ballet flats for a chic warm-weather look.
Inherently glamorous—perhaps due to the voluminous shape that feels synonymous with the silhouettes debuted in Christian Dior's iconic "New Look" collection of 1947—this skirt trend offers an easy way to give your outfits an elegant overhaul.
To shop the skirt that feels just as relevant now as it did nearly 80 years ago, read on to discover our edit of the best circle skirts below.
SHOP CIRCLE SKIRTS:
This subtle burgundy shade pairs so well with brighter spring colours, such as baby blue and light pink.
This features an elasticated waistband for a relaxed and comfortable fit.
Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.
With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.
-
Not a Mini and Not a Midi—This Trending '90s Skirt Style Is Far More Controversial
Elizabeth Olsen is on board.
By Allyson Payer
-
I Used to Hate This Skirt Trend, But Lucy Boynton's Cute Outfit Made Me Do a 180
True prep.
By Drew Elovitz
-
This Elegant Skirt Trend Resurfacing Just in Time for Spring Was Destined to Happen
Follow Zoë Kravitz's lead.
By Nikki Chwatt
-
It's Starting to Look Like This Skirt Color Will Upend Last Year's White-Skirt Trend
Ready for a change?
By Allyson Payer
-
Kendall Jenner Wore the Trend Everyone With Taste Is Wearing in 2025
A more formal take on model-off-duty style.
By Emma Spedding
-
Katie Holmes Is Signaling the Return of This Pretty '90s Skirt Trend
By Allyson Payer
-
This Dated Dress Trend Is Officially Everywhere Again (Like We Predicted)
Shop the style inside.
By Michelle Scanga
-
Quiet Luxury's Out—Here's How Stylish Women Are Wearing Loud Luxury's First Viral Trend
It's too chic.
By Copelyn Bengel