Fashion People are Swapping Polka Dot Skirts For Timeless Checked Styles

Collage of influencers wearing checked skirts with t-shirts, knits and suede jackets.

(Image credit: @chloekathbutler, @nlmarilyn, @holliemercedes)

published 21 September 2025

I, like so many others, was well and truly swept up in the polka-dot craze of the summer. Playful, peppy and easy to style, that print injected a dose of energy into my warm-weather wardrobe. But with autumn now nipping at summer’s heels, I’ve been on the lookout for a cool-weather upgrade to step in where my beloved polka dots once shone, and the checked skirt trend has quickly become the season’s frontrunner.

An autumn-ready evolution, checks carry with them a heritage-tinged moodiness that feels perfectly at home in cooler weather. Perhaps it’s their link to traditional Scottish tartans, but the pattern seems to hold an innate cold-weather energy that becomes irresistible once the seasons shift. Cast in the season’s favourite silhouettes—the swishy, feminine skirt—the effect feels at once familiar and contemporary. Think collegiate charm meets daily wearability.

Influencer @nlmarilyn wears COS wrap checked skirt.

Already, I’ve spotted the trend across my feed. Influencers are wearing theirs with simple tees while the weather is still mild, but I'm more excited to see these skirts transition into the depths of autumn and winter. Picture them styled with oversized knits, belted blazers, or layered under leather jackets. And when the chill really sets in, chunky knee-high boots or biker styles will lend the right amount of edge.

Influencer @chloekathbutler wears a red checked skirt.

Heritage labels such as Burberry have always championed the print, but this season has seen a surge of fresh adopters. S.S. Daley, for instance, wove check skirts into his debut womenswear collection, proving their poignance right now. On the high street, COS' Draped Checked Midi Skirt has become a New York Fashion Week favourite, while H&M and Anthropologie have embraced the trend with gusto, too.

Influencer @holliemercedes wears a checked skirt with a light brown suede jacket and black square-toe boat shoes.

Read on for my edit of the best checked skirts to shop now.

Shop Checked Skirts:

H&M

Circular Cotton Skirt

I recommend you act quickly. This won't stay in stock for long.

COS

Draped Checked Midi Skirt

Shop the chic skirt influencer @nlmarilyn is already wearing.

Anthropologie

Seamed Plaid Wrap Maxi Skirt

Style with a white tee or wear with a slouchy knit.

Burberry

Check Wool Blend Midi Kilt

This might be an investment buy, but it's one you'll get wear out of autumn after autumn.

Anthropologie

Basque Waist Check Midi Skirt

Style with knee-high boots or give it a pretty spin by pairing with mary janes.

House of Sunny

Retro Check Mesh Skirt

Wear this with the matching top to double-down on the growing checked trend.

Topshop

Full Circle Maxi Skirt

The full circle cut gives this a dramatic energy that can entirely energise an autumn look.

SS Daley

Kate' Sheer Argyle Pleated Skirt

Style with tall biker boots and a thick knit to bring this sheet skirt into the autumn months.

Damson Madder

Josie Midi Skirt

While I love this in the checked design, this also comes in a plain olive green design.

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.