Skip to main content
The Simons members:
free shipping over $50 and free returns (exceptions may apply)

Men's Check & Plaid Shirts

Check brushed overshirt discounted price Can$89.00
Point Zero
Checkered flannel shirt
Slim fit
discounted price Can$59.00
Only & Sons
Lightweight cotton check shirt discounted price Can$60.00
Jack & Jones
Canadian overshirt discounted price Can$145.00
Hooké
Caramel check flannel shirt discounted price Can$95.00
Wrangler
Red check flannel shirt discounted price Can$95.00
Wrangler

New

Tartan jacquard flannel shirt discounted price Can$275.00
Outclass
Blue check Oxford shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren

New

Woodland heritage-check shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren

New

Tricolour check flannel shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren
Tricolour check Oxford shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren
Blue check flannel shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren
Plaid Oxford shirt discounted price Can$175.00
Polo Ralph Lauren
Gingham Oxford shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren
Flannel checkered shirt discounted price Can$175.00
Polo Ralph Lauren

New

Small check shirt
Classic fit
discounted price Can$175.00
Polo Ralph Lauren

New

Fall check knit overshirt discounted price Can$310.00
Wax London

New

Dabyn plush-lined check overshirt discounted price Can$348.00
Robert Barakett
Indigo check overshirt discounted price Can$238.00
Scotch & Soda

New

Banker-stripe flannel shirt discounted price Can$150.00
FIVE STUDIOS
Frayed-hem check shirt discounted price Can$350.00
Found
Embroidered logo tartan shirt discounted price Can$295.00
Paul Smith X Barbour
Flannel check overshirt regular price $99.00 discounted price Can$69.00
Djab
Flannel check overshirt regular price $99.00 discounted price Can$69.00
Djab

New

Bigwig check shirt discounted price Can$125.00
Obey

New

Bigwig Jack mini-check shirt discounted price Can$130.00
Obey

New

Shadow check brushed flannel shirt discounted price Can$500.00
Ecole de Pensée
Gingham flannel shirt discounted price Can$495.00
Emporio Armani
Checkered seersucker shirt discounted price Can$350.00
PS Paul Smith

New

Fluid plaid flannel shirt discounted price Can$425.00
Séfr

Flannel and Plaid Shirts for Men

Comfortably layer up with soft and rugged flannel shirts, perfect for cooler, crisp days and laid-back looks. Whether worn open over a tee or buttoned up, they bring warmth and effortless style to your wardrobe.

Add a touch of classic pattern with our collection of plaid shirts, available in a range of colours and fits. Ideal for weekend wear or casual Fridays, they're a go-to for those who love a timeless, relaxed vibe.

For something fresh and versatile, explore our check shirts for men—a staple for smart-casual dressing. Whether paired with denim or chinos, they offer an easy way to stay sharp and dressy without sacrificing comfort.

Flag of the United States

Are you in the United States?

Visit simons.com