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

Men's Check & Plaid Shirts

New

Modern check shirt
Relaxed fit
discounted price Can$69.00
Lindbergh

New

Textured check overshirt discounted price Can$135.00
Lindbergh

New

Micro-check shirt
Regular fit
discounted price Can$69.00
Lindbergh

New

Neutral mini check shirt
Regular fit
discounted price Can$69.00
Lindbergh
Lightweight cotton check shirt discounted price Can$60.00
Jack & Jones
Canadian overshirt discounted price Can$145.00
Hooké

New

Caramel check flannel shirt discounted price Can$95.00
Wrangler
Red check flannel shirt discounted price Can$95.00
Wrangler
Earthy check shirt discounted price Can$120.00
FIVE STUDIOS
Blue check Oxford 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
Indigo check overshirt discounted price Can$238.00
Scotch & Soda

New

Frayed-hem check shirt discounted price Can$350.00
Found
Relaxed plaid shirt discounted price Can$499.00
BOSS

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.