Check Mate: Nine new ways to square off with plaid, tartan and tweed

It’s not what you wear, as the adage goes, but how you wear it. So, get ready to dress outside the lines. Here’s how.

Thu, 06 Nov, 2025 - 17:31

Annmarie O’Connor

The mathematical rigour of checks are not the stuff of disorderly conduct. Yet their association with punk, grunge and Vivienne Westwood pirates is legendary.

Plaid, tartan and tweed may bear the hallmark of heritage but their reputation for stylish subversion proceeds them. Perhaps that’s the appeal.

It’s not what you wear, as the adage goes, but how you wear it. So, get ready to dress outside the lines. Here’s how.

Helen McAlinden’s ‘Beryl’ herringbone tweed coat sets the tone: a tailored epic that plays by the rules but also knows how to break them. Hint: a leather dress instantly changes the dynamic.

Equally, Russell & Bromley’s ‘Ravensmoor’ boots, made from richly woven silk, give buccaneer swagger for those who like a side of anarchy with their accessories.

Prefer something softer? Inspired by the '70s, House of Sunny’s retro blanket jacket leans into duffle nostalgia with its playful toggles and matching scarf while Essentiel Antwerp’s draped skirt brings a sculptural twist to traditional tartan.

Pair with scraped back hair, a black roll neck and matching over-the-knee boots for best results.

If luxe-minimalism is your love language, the checked alpaca-blend jumper at COS is a strong contender when partnered with burgundy patent leather.

For everyday impact, layer M&S Collection’s trio of matching plaid separates, especially with a leather jacket and biker boots.

Then again, the iconic check shirt always wins big, like H&M’s fitted version - a shoo-in with barrel leg jeans and slingbacks for drinks at your local.

Sometimes simplicity is the biggest act of anarchy. No one expects it.

GET THE LOOK

A model presents a creation by Vivienne Westwood for the Womenswear Ready-to-wear Fall-Winter 2025/2026 collection as part of the Paris Fashion Week, in Paris on March 8, 2025. (Photo by Bertrand GUAY / AFP) (Photo by BERTRAND GUAY/AFP via Getty Images)

1. A model presents a creation by Vivienne Westwood for the Womenswear Ready-to-wear Fall-Winter 2025/2026 collection as part of the Paris Fashion Week, in Paris on March 8, 2025.