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

Men's Check & Plaid Shirts

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
Check knit camp shirt
Relaxed fit
regular price $69.00 discounted price Can$19.99
Only & Sons
Small check shirt regular price $79.00 discounted price Can$49.95
Only & Sons
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

New

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
Gordon windowpane check shirt
Regular fit
regular price $155.00 discounted price Can$79.95
Barbour
Indigo check overshirt discounted price Can$238.00
Scotch & Soda
Relaxed plaid shirt discounted price Can$499.00
BOSS
Lightweight mini-check shirt
Imported from Seoul
regular price $89.00 discounted price Can$69.95
Le 31
Windowpane check lightweight shirt
Imported from Seoul
regular price $99.00 discounted price Can$69.95
Le 31
Burgundy check flannel shirt
Imported from Seoul
regular price $125.00 discounted price Can$39.95
Le 31
Magnus micro-check shirt regular price $59.00 discounted price Can$39.95
Redefined rebel

Editor's pick

Plaid seersucker shirt
Boxy fit
regular price $69.00 discounted price Can$19.99
Djab

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.