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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.