Fashion’s highland fling is by no means anything new. Luxury houses have been using tartan, plaids and checks to lend collections a sense of heritage and toughness for decades (see Vivienne Westwood’s punkish tartans and Alexander McQueen’s romanticised Highland codes to more recent takes from Dior and Chanel).
Come summer, gingham and whimsical checks tend to illuminate breezy cotton dresses, bringing a playful, picnic-ready feel to the warmer months. But as autumn arrives, the fabrics get thicker, the colourways earthier, and the checked dress truly comes into its own.
The autumn/winter 2026 collections provided ample styling inspiration. At Chloé, a blue and yellow tiered maxi dress came wafting down the runway in wispy chiffon, styled with camel suede boots and sepia-toned sunglasses with a distinctly ’70s feel. Moschino played with the same zesty colour pairing, applying checks to a silk button-down dress, styled with trailing silk scarves. Elsewhere, Loewe focused on sculptural silhouettes, with a short checked dress finished with a dramatic bow at the neck, while Dries Van Noten has a grungier take with a moss-hued halterneck dress with a gathered bubble hem, grounded with black leather boots.
Of course, you don’t need to go full Highland fling to get in on the trend. For a more casual take, try wearing an oversized men’s plaid shirt as a dress, cinching it at the waist or leaving it loose over knee-high boots. Alternatively, layer a checked cotton midi under a fine-knit jumper and add loafers or ballet flats for an easy everyday look. When the temperature drops, look to heavier wool-blend styles and darker tartans that feel suitably autumnal.
Whether you prefer traditional tartan, playful plaid or oversized checks, there’s a version for every autumn wardrobe. From easy day dresses to statement wool styles, scroll on to discover the best checked dresses to shop now.
The checked mini
Sunday Draped Checked Wool-Blend Minidress
The cotton midi
Pure Cotton Checked V-Neck Midi Waisted Dress
The floaty maxi
Fernanda Ruffle Tiered Checked Silk-Satin Maxi Dress
The draped dress
Twisted Draped Checked Cotton Midi-Dress
