Skip to main content
Free shipping over $50 for The Simons members
& Easy returns: $9.99 flat fee (exceptions may apply)

Boxers & Briefs

Featured

Editor's pick

Red boxer brief
DROPTEMP™
discounted price US$30.00
Saxx
Repeated logo briefs
3-pack
discounted price US$50.00
Lacoste
Classic microfibre trunks
3-pack
discounted price US$55.00
Calvin Klein
Loose eco-friendly flannel boxer regular price $25.00 discounted price US$19.99
Le 31
Loose eco-friendly flannel boxer regular price $25.00 discounted price US$19.99
Le 31
Loose eco-friendly flannel boxer regular price $25.00 discounted price US$19.99
Le 31
Microfibre athletic boxer brief regular price $15.00 discounted price US$9.99
Le 31
Festive trunk regular price $20.00 discounted price US$14.99
Only & Sons
Festive trunk regular price $20.00 discounted price US$14.99
Only & Sons
Monochrome trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Two-tone trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful-waist navy trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Solid viscose trunk discounted price US$19.00
Le 31
Solid viscose trunk discounted price US$19.00
Le 31
Solid viscose trunk discounted price US$19.00
Le 31

Editor's pick

Favourite snacks trunk regular price $19.00 discounted price US$14.99
Le 31

Editor's pick

Favourite snacks trunk regular price $19.00 discounted price US$14.99
Le 31
Favourite snacks trunk regular price $19.00 discounted price US$9.99
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Solid and striped essential boxer briefs
2-pack
regular price $35.00 discounted price US$24.95
Le 31
Mixed stripe viscose trunk regular price $20.00 discounted price US$14.99
Le 31
Winter pattern trunk regular price $19.00 discounted price US$14.99
Le 31
Scale-look trunk regular price $19.00 discounted price US$14.99
Le 31
Mini diamond trunk regular price $19.00 discounted price US$14.99
Le 31
Red stripe trunk regular price $19.00 discounted price US$14.99
Le 31
Heathered turquoise trunk regular price $19.00 discounted price US$14.99
Le 31
Striped grey trunk regular price $19.00 discounted price US$14.99
Le 31
Organic cotton mesh trunk discounted price US$19.99
Le 31
Solid and printed trunks
2-pack
regular price $30.00 discounted price US$19.99
Le 31
Tone-on-tone Feel Lyocell trunk discounted price US$25.00
2 for $39.95
Le 31
Tone-on-tone Feel Lyocell boxer brief discounted price US$25.00
2 for $39.95
Le 31

Editor's pick

Contrast-seam boxer brief regular price $15.00 discounted price US$9.99
Le 31
Colourful organic cotton and modal boxer briefs
3-pack
regular price $40.00 discounted price US$24.95
Le 31
Solid boxer briefs
6-pack
regular price $44.95 discounted price US$29.95
Le 31
Scale-look brief regular price $19.00 discounted price US$14.99
Le 31
Mini diamond brief regular price $19.00 discounted price US$14.99
Le 31
Heathered turquoise brief regular price $19.00 discounted price US$14.99
Le 31
Striped grey brief regular price $19.00 discounted price US$14.99
Le 31
Red stripe brief regular price $19.00 discounted price US$14.99
Le 31
Tone-on-tone Feel lyocell brief discounted price US$25.00
2 for $39.95
Le 31
Contrast-seam solid brief regular price $19.00 discounted price US$14.99
Le 31
Twin-stripe brief regular price $19.00 discounted price US$14.99
Le 31
Organic cotton mesh brief discounted price US$19.99
Le 31
Organic cotton briefs
3-pack
discounted price US$25.00
Le 31
Organic cotton mesh cami regular price $30.00 discounted price US$19.99
Le 31

Sophisticated menswear with a touch of avant-garde, Le 31 appeals to the businessman, the innovator, the adventure-seeker, and the athlete with its wide range of collections that feature everything from the comfiest essentials to the season's trendiest pieces.

Contrasting topstitch trunk discounted price US$15.00
Le 31
Contrasting topstitch trunk discounted price US$15.00
Le 31
Contrasting topstitch trunk discounted price US$15.00
Le 31
Bright organic cotton trunk regular price $19.00 discounted price US$14.99
Le 31
Bright organic cotton trunk regular price $19.00 discounted price US$14.99
Le 31
Bright organic cotton trunk regular price $19.00 discounted price US$14.99
Le 31
Jack & Jones at Simons

Founded in 1990 out of a love for denim, this European brand offers a complete range of clothing, underwear, and accessories for men.

Solid microfibre trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Retro logo trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Biker skeleton trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Neon contrast trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Funky pattern trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Touch-of-blue trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful waist microfibre trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Solid blue trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Vibrant colour trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Festive jungle trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful garden trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful skull trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Surrealist illustration trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Colourful band black trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Minimalist solid trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Pink flamingo trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Red-trim solid trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Vibrant jungle trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Vibrant leaf trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Contrast writing trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Two-tone logo trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Signature waist trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Logo waist trunk discounted price US$15.00
3 for $34.95
Jack & Jones
Tropical trunk discounted price US$15.00
Jack & Jones

Canadian Brand | Founded in Vancouver in 2006, this underwear company looks to improve men's day-to-day with comfort technology that's tried and true.

Colourful illustration boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx
Face Melter boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx
Hot sauce brief
DAYTRIPPER
discounted price US$25.00
Saxx
Office Party boxer brief
DAYTRIPPER
discounted price US$25.00
Saxx
Brain Freeze boxer brief
DROPTEMP™
regular price $30.00 discounted price US$24.95
Saxx
Banana Split boxer brief
DROPTEMP™
discounted price US$30.00
Saxx
Starry Surf boxer brief
DROPTEMP™
regular price $30.00 discounted price US$24.95
Saxx
Black boxer brief
DROPTEMP™
regular price $30.00 discounted price US$24.95
Saxx
Neutral boxer briefs
DROPTEMP™ - 3-pack
discounted price US$79.00
Saxx
Logo waist solid trunk
VIBE
discounted price US$30.00
Saxx
Brown boxer brief
VIBE
discounted price US$30.00
Saxx
Winter Skies boxer brief
VIBE
discounted price US$30.00
Saxx
Geo-patterned boxer brief
VIBE
discounted price US$30.00
Saxx
Snowmobile yeti boxer brief
VIBE
discounted price US$30.00
Saxx
Heathered-stripe boxer brief
VIBE
regular price $30.00 discounted price US$14.99
Saxx
Animal hockey player boxer brief
VIBE
discounted price US$30.00
Saxx
Bear boxer brief
VIBE
discounted price US$30.00
Saxx
Hot dog boxer brief
VIBE
discounted price US$30.00
Saxx