A Classic Shirt
With a Dark Side
Shadow plaid shirts bring subtle style and laid-back edge to your wardrobe
Few items capture the laid-back, layered vibe of fall quite like a good plaid shirt. And this season, the shadow plaid is the one stylish guys are reaching for—a hardwearing wardrobe workhorse and the very definition of a layering piece. Popularized in the '90s and now making a strong comeback, these ombré-style checks trade bold contrast for hazy gradients and tonal colors, resulting in a look that's less lumberjack and more laid-back cool.
Part of the shadow plaid's appeal is its versatility. Button it up for a clean, modern feel. Leave it open over a T-shirt or thermal for a casual, textured layer. Tuck it into worn-in jeans, pair it with some wide-leg trousers, or throw it on with Dickies workwear pants—the softer palette plays well with just about anything. From chore shirts to more tailored cuts to Western styles, the best versions right now lean into textured materials and slightly roomier silhouettes that invite layering without bulk.
While the throwback vibe is undeniable—think Eddie Vedder on stage or skaters posted up on the curb—today's iterations are more refined. Brands are swapping stiff weaves for softer, more sustainable fabrics and fresh colorways. Whether you splurge on a heritage piece or score an affordable find, a shadow plaid shirt is an easy way to nod to nostalgia while keeping your fall wardrobe current.
The Best
Shadow Plaid Shirt
Benoit flannel shirt,
$435 by Officine Générale
Checked flannel shirt,
$39.90 by UNIQLO
What to Look For
Since they can sub in for outerwear, you want something substantial—that means a thicker fabric, sturdy buttons and quality stitching. And that soft, fluffy texture? It’s created by running a fine metal comb over the fabric (before or after weaving). Flannel shirts may be left without brushing, completely brushed, or even brushed on select sides for extra coziness.
Palomino plaid shirt,
$168 by Buck Mason
Melange shadow plaid shirt,
$198 $198 / $62.50 by Billy Reid
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Wool flannel shirt,
$179 by Pendleton
Cotton flannel,
$268 / $99 by Frame
Brushed cotton overshirt,
$59.90 by JW Anderson for UNIQLO
Shadow check shirt,
$245 / $125 by Corridor
Cotton-hemp twill shirt,
$118 by J.Crew
How to Wear It
Off-Duty
Throw it open over a white tee with black jeans and sneakers for a low-effort weekend uniform.
Workday Casual
Tuck it into dark chinos, add a belt and loafers—office-ready without losing comfort.
Night Out
Buttoned up with tailored trousers and Chelsea boots for a subtle mix of rugged and refined.
Layered Up
Wear it under a chore coat or denim jacket with a chunky knit scarf for crisp mornings.
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