How To Style A Checked Shirt Like A Fashion Insider

Checked shirts generally call to mind ’90s grunge and clean-cut Americana; they are one part Kurt Cobain and one part Brad Pitt. For fall/winter ’25, however, brands from Burberry to Isabel Marant proved that plaid can be very chic. Re-emerging in line with the British heritage trend that’s been bubbling for a few seasons now – its roots stretch back to early tartan patterns in Scotland, where checks signified clan identity – the checked shirt is also a key piece in the recent obsession with all things Western-coded.

This season, the trick is to incorporate this style into your current wardrobe – alongside tailoring, leather and denim – to achieve more of a polished feel. Suede is another natural partner to tartan, and our fashion team have fallen hard for Dutch, family-run brand Arma, which specializes in timeless suede and leather pieces. Consider its ‘Kaylee’ jacket, which comes in an oversized fit that is perfect for layering over a checked shirt in matching neutral hues. Actor Ilfenesh Hadera took her styling cues from the Kallmeyer runway by knotting the New York-based brand’s plaid shirt around the waist of tailored pants, as it was in the show.

Vogue Italia’s Marta Oldrini, meanwhile, put a ’90s spin on hers by shrugging it on over a gray T-shirt and baggy pants and loading up on gold chains (opening image, center). Put your own twist on this look with Polo Ralph Lauren’s flannel shirt layered over Aimé Leon Dore’s logo tee and Agolde’s wide-leg ‘Keira’ jeans, finishing with Gucci’s classic ‘Horsebit’ loafers to keep things suitably sophisticated.

The street-style set also demonstrated how checked shirts can be styled in more unexpected ways, either layered across the shoulder or tucked into midi skirts. Button up Proenza Schouler’s iteration and tuck it into Dries Van Noten’s sleek pencil skirt, adding TWP’s trench coat and Alaïa’s ‘Le Click’ bag for a perfectly pulled-together office look. For evening, Isabel Marant’s ‘Bruna’ shirt from the fall/winter ’25 runway will look effortlessly cool with Jacquemus’s Capri shorts, Saint Laurent’s glossy leather mules and Alaïa’s sculptural hoop earrings. Of course, if you do want to wear yours with your favorite jeans and cowboy boots, we are totally here for that, too.