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

Men's Comfort Fit Dress Shirts

Comfort Fit

A straight cut with room to move in the waist, shoulders, and sleeves.

Comfort fit shirt
Le 31
Quick view Full details
Blue mini-gingham shirt
Comfort fit regular price $125.00 discounted price Can$69.95
Le 31
Quick view Full details
Jacquard striped bib tuxedo shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Contrast stripe shirt
Modern fit regular price $175.00 discounted price Can$99.95
Olymp
Quick view Full details
Green stripe shirt
Modern fit regular price $150.00 discounted price Can$99.95
Olymp
Quick view Full details
Brick-red striped shirt
Comfort fit regular price $125.00 discounted price Can$49.95
Le 31
Quick view Full details
Solid twill wrinkle-free shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details
Organic cotton floral geometry shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Dotwork medallion shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Blue flowering shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Blue geo mosaic shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Spring garden shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Contrasting mini-star shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Blue and brown gingham shirt
Comfort fit regular price $79.00 discounted price Can$49.95
Le 31
Quick view Full details
Solid floral-trim shirt
Comfort fit
Made with Liberty Fabric regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Solid floral-trim shirt
Comfort fit
Made with Liberty Fabric regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Floral-print shirt
Comfort fit regular price $79.00 discounted price Can$29.95
Le 31
Quick view Full details
Satiny 100% cotton shirt
Comfort fit discounted price Can$79.00
Le 31
Quick view Full details
French cuff sateen shirt
Comfort fit discounted price Can$79.00
Le 31
Quick view Full details
Dobby stretch shirt
Comfort fit discounted price Can$125.00
Le 31
Quick view Full details

New

Stretch lightweight shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details

New

Stretch lightweight shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details

New

Double stripe shirt
Comfort fit discounted price Can$125.00
Le 31
Quick view Full details
Darkened rose shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details
Floral shadow shirt
Comfort fit regular price $99.00 discounted price Can$69.95
Le 31
Quick view Full details
Floral silhouette shirt
Comfort fit regular price $99.00 discounted price Can$69.95
Le 31
Quick view Full details
Contrast abstract flower shirt
Comfort fit regular price $99.00 discounted price Can$69.95
Le 31
Quick view Full details
Denim-blue striped shirt
Comfort fit regular price $99.00 discounted price Can$49.95
Le 31
Quick view Full details

New

Triple-stripe shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details

New

Mini-houndstooth shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details

New

Clay stripe shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Bistre painterly floral shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Dark floral shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Taupe gingham shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Chevron jacquard shirt
Comfort fit discounted price Can$150.00
Le 31
Quick view Full details
Monochrome ultra-stretch shirt
Comfort fit discounted price Can$195.00
Klauss Boehler
Quick view Full details
Fluid two-tone twill performance shirt
Comfort fit regular price $195.00 discounted price Can$99.95
Klauss Boehler
Quick view Full details
Fluid two-tone twill performance shirt
Comfort fit regular price $195.00 discounted price Can$99.95
Klauss Boehler
Quick view Full details
Minimalist performance shirt
Regular fit regular price $95.00 discounted price Can$49.95
Selected
Quick view Full details

New

Pure cotton Dobby shirt
Regular fit discounted price Can$95.00
Selected
Quick view Full details

New

Pure cotton Dobby shirt
Regular fit discounted price Can$95.00
Selected
Quick view Full details
Solid twill wrinkle-free shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details
Solid twill wrinkle-free shirt
Comfort fit discounted price Can$99.00
Le 31
Quick view Full details
Two-tone pinstriped shirt
Comfort fit regular price $125.00 discounted price Can$49.95
Le 31
Quick view Full details
Tennis ball and racket shirt
Modern fit regular price $150.00 discounted price Can$49.95
Olymp
Quick view Full details
Two-tone diamond shirt
Modern fit regular price $150.00 discounted price Can$49.95
Olymp
Quick view Full details
Colourful mini-flower shirt
Modern fit regular price $175.00 discounted price Can$49.95
Olymp
Quick view Full details
Blue foliage stretch shirt
Regular fit regular price $195.00 discounted price Can$49.95
Klauss Boehler