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

Men's Pyjama Sets

Underwear & Leisurewear

FEATURED

Quick view Full details
Pink and grey check pyjama set regular price $75.00 discounted price Can$49.95
Majestic
Quick view Full details
Morning teddy bear pyjama set discounted price Can$130.00
Polo Ralph Lauren
Quick view Full details
Morning teddy bear pyjama set discounted price Can$130.00
Polo Ralph Lauren
Quick view Full details
Blue heather piped pyjama set discounted price Can$295.00
Polo Ralph Lauren
Quick view Full details
Minimalist check pyjama set discounted price Can$80.00
Majestic
Quick view Full details
Minimalist check pyjama set discounted price Can$80.00
Majestic

Cue “Relaxation Mode”

Unwind in style with our matching loungewear separates.

Man wearing loungewear
+2
Quick view Full details
Soft solid T-shirt discounted price Can$29.00
Le 31
+2
Quick view Full details
Brushed jersey pyjama short discounted price Can$35.00
Le 31
Quick view Full details
Breakfast print T-shirt regular price $29.00 discounted price Can$19.99
Le 31
+2
Quick view Full details
Soft solid T-shirt discounted price Can$29.00
Le 31
Quick view Full details

Editor's pick

Solid brushed finish pyjama pant discounted price Can$39.00
Le 31
Quick view Full details
Breakfast print T-shirt regular price $29.00 discounted price Can$19.99
Le 31
Quick view Full details
Breakfast print T-shirt regular price $29.00 discounted price Can$19.99
Le 31
+2
Quick view Full details
Brushed jersey pyjama short discounted price Can$35.00
Le 31
Quick view Full details
Breakfast print T-shirt regular price $29.00 discounted price Can$19.99
Le 31
+2
Quick view Full details
Brushed jersey pyjama short discounted price Can$35.00
Le 31
+2
Quick view Full details
Soft solid T-shirt discounted price Can$29.00
Le 31
Quick view Full details

Editor's pick

Solid brushed finish pyjama pant discounted price Can$39.00
Le 31
+2
Quick view Full details
Brushed jersey pyjama short discounted price Can$35.00
Le 31
+2
Quick view Full details
Soft solid T-shirt discounted price Can$29.00
Le 31
Quick view Full details

Editor's pick

Solid brushed finish pyjama pant discounted price Can$39.00
Le 31
+2
Quick view Full details
Brushed jersey pyjama short discounted price Can$35.00
Le 31
+2
Quick view Full details
Soft solid T-shirt discounted price Can$29.00
Le 31
Quick view Full details

Editor's pick

Solid brushed finish pyjama pant discounted price Can$39.00
Le 31
Quick view Full details
Solid TENCEL™ modal pyjama short discounted price Can$39.00
Le 31
Quick view Full details
Solid TENCEL™ modal T-shirt discounted price Can$39.00
Le 31
Quick view Full details
Fluid TENCEL™ modal pyjama pant discounted price Can$59.00
Le 31
Quick view Full details
Lightweight solid linen shirt regular price $79.00 discounted price Can$39.95
Le 31
Quick view Full details
Solid lightweight linen pyjama pant regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Solid lightweight linen pyjama short regular price $69.00 discounted price Can$49.95
Le 31
Quick view Full details
Solid lightweight linen pyjama short regular price $69.00 discounted price Can$49.95
Le 31
Quick view Full details
Lightweight solid linen shirt regular price $79.00 discounted price Can$39.95
Le 31
Quick view Full details
Solid lightweight linen pyjama pant regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Striped lightweight linen pyjama pant regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Striped lightweight linen shirt regular price $79.00 discounted price Can$39.95
Le 31
Quick view Full details
Lightweight striped linen pyjama short regular price $69.00 discounted price Can$49.95
Le 31
Quick view Full details
Lightweight striped linen pyjama short regular price $69.00 discounted price Can$49.95
Le 31
Quick view Full details
Striped lightweight linen pyjama pant regular price $89.00 discounted price Can$69.95
Le 31
Quick view Full details
Striped poplin shirt regular price $59.00 discounted price Can$29.95
Le 31
Quick view Full details
Striped poplin pyjama pant regular price $59.00 discounted price Can$29.95
Le 31
Quick view Full details
Patterned poplin pyjama short regular price $49.00 discounted price Can$29.95
Le 31
Quick view Full details
Little dog poplin pyjama short
In support of the Mira Foundation discounted price Can$49.00
Simons x Mira
Quick view Full details
Dog ultra-comfortable T-shirt
In support of the Mira Foundation discounted price Can$39.00
Simons x Mira
Quick view Full details
Dog ultra-comfortable T-shirt
In support of the Mira Foundation discounted price Can$39.00
Simons x Mira
Quick view Full details
Solid stretch lounge short regular price $59.00 discounted price Can$39.95
BOSS
Quick view Full details
Solid stretch T-shirt regular price $59.00 discounted price Can$39.95
BOSS
Quick view Full details
Solid waffle pyjama short discounted price Can$69.00
BOSS
Quick view Full details
Embroidered logo waffle T-shirt discounted price Can$69.00
BOSS
Quick view Full details
Embroidered-logo waffle pyjama short discounted price Can$69.00
BOSS
Quick view Full details
Waffled pyjama joggers discounted price Can$99.00
BOSS
Quick view Full details
Embroidered logo waffle T-shirt discounted price Can$69.00
BOSS
Quick view Full details
Embroidered-logo waffle pyjama short discounted price Can$69.00
BOSS
Quick view Full details
Waffled pyjama joggers discounted price Can$99.00
BOSS
Quick view Full details
Monochrome T-shirt regular price $59.00 discounted price Can$39.95
BOSS
Quick view Full details
Two-tone lounge joggers discounted price Can$89.00
BOSS
Quick view Full details
Monochrome T-shirt regular price $59.00 discounted price Can$39.95
BOSS
Quick view Full details
Two-tone lounge joggers discounted price Can$89.00
BOSS
Quick view Full details
Monochrome T-shirt regular price $59.00 discounted price Can$39.95
BOSS
Quick view Full details
Comfortable khaki pyjama joggers discounted price Can$89.00
BOSS
Quick view Full details
Neutral ultra-comfortable T-shirt discounted price Can$59.00
BOSS
Quick view Full details
Sand ultra-comfortable pyjama short discounted price Can$59.00
BOSS
Quick view Full details
Embroidered-logo sand comfort jacket regular price $99.00 discounted price Can$69.95
BOSS
Quick view Full details
Embroidered-logo sand lounge joggers regular price $89.00 discounted price Can$69.95
BOSS
Quick view Full details
Minimalist check pyjama set discounted price Can$80.00
Majestic
Quick view Full details
Minimalist check pyjama set discounted price Can$80.00
Majestic
Quick view Full details
Pink and grey check pyjama set regular price $75.00 discounted price Can$49.95
Majestic
Quick view Full details
Morning teddy bear pyjama set discounted price Can$130.00
Polo Ralph Lauren
Quick view Full details
Morning teddy bear pyjama set discounted price Can$130.00
Polo Ralph Lauren
Quick view Full details
Blue heather piped pyjama set discounted price Can$295.00
Polo Ralph Lauren
Quick view Full details
Blue hue poplin shirt discounted price Can$85.00
Polo Ralph Lauren
Quick view Full details
Blue-toned poplin pyjama pant discounted price Can$95.00
Polo Ralph Lauren
Quick view Full details
Striped shirt regular price $79.00 discounted price Can$49.95
Pockies
Quick view Full details
Striped pyjama pant regular price $79.00 discounted price Can$49.95
Pockies
Quick view Full details
Light pink poplin shirt regular price $100.00 discounted price Can$49.95
Pockies
Quick view Full details
Light pink poplin pyjama pant regular price $100.00 discounted price Can$49.95
Pockies
Quick view Full details
Brown and blue striped crisp poplin shirt regular price $225.00 discounted price Can$149.95
Rue de Tokyo
Quick view Full details
Brown striped crisp poplin pyjama short regular price $205.00 discounted price Can$149.95
Rue de Tokyo
Quick view Full details
Sergei striped seersucker kimono shirt regular price $250.00 discounted price Can$149.95
Rue de Tokyo
Quick view Full details
Paxton striped seersucker pyjama pant regular price $245.00 discounted price Can$149.95
Rue de Tokyo
Quick view Full details
Skyler striped seersucker shirt regular price $245.00 discounted price Can$149.95
Rue de Tokyo
Quick view Full details
Hessel pinstriped poplin shirt discounted price Can$310.00
Tekla
Quick view Full details
Hessel pinstriped poplin pyjama pant discounted price Can$260.00
Tekla
Quick view Full details
Oatmeal and chocolate striped poplin shirt discounted price Can$310.00
Tekla
Quick view Full details
Oatmeal and chocolate striped poplin pyjama pant discounted price Can$260.00
Tekla
Quick view Full details
Striped organic cotton poplin shirt discounted price Can$310.00
Tekla
Quick view Full details
Striped organic cotton poplin pyjama pant discounted price Can$260.00
Tekla
Quick view Full details

New

Lanegan lightweight check shirt discounted price Can$310.00
Tekla
Quick view Full details

New

Lanegan lightweight check pyjama pant discounted price Can$260.00
Tekla
Quick view Full details
Striped poplin pyjama short discounted price Can$195.00
Tekla
Flag of the United States

Are you in the United States?

Visit simons.com