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

Men's Long Leg Boxer Briefs

Underwear & Leisurewear
Solid and striped essential boxer briefs
2-pack regular price $40.00 discounted price Can$29.95
Le 31
Solid and striped essential boxer briefs
2-pack regular price $40.00 discounted price Can$29.95
Le 31
Solid and striped essential boxer briefs
2-pack regular price $40.00 discounted price Can$29.95
Le 31
Tone-on-tone Feel Lyocell boxer brief discounted price Can$29.00
2 for $39.95
Le 31
Colourful organic cotton and modal boxer briefs
3-pack regular price $45.00 discounted price Can$29.95
Le 31
Colourful organic cotton and modal boxer briefs
3-pack regular price $45.00 discounted price Can$29.95
Le 31
Colourful illustration boxer brief
DAYTRIPPER discounted price Can$29.00
Saxx
Face Melter boxer brief
DAYTRIPPER discounted price Can$29.00
Saxx
Hot sauce brief
DAYTRIPPER discounted price Can$29.00
Saxx

New

Office Party boxer brief
DAYTRIPPER discounted price Can$29.00
Saxx
Pixel and solid boxer briefs
DAYTRIPPER - 2-pack discounted price Can$52.00
Saxx
Blue and solid boxer briefs
DAYTRIPPER - 2-pack discounted price Can$52.00
Saxx
Brain Freeze boxer brief
DROPTEMP™ regular price $37.00 discounted price Can$29.95
Saxx
Banana Split boxer brief
DROPTEMP™ discounted price Can$37.00
Saxx
Starry Surf boxer brief
DROPTEMP™ regular price $37.00 discounted price Can$29.95
Saxx
Water Whirled boxer brief
DROPTEMP™ regular price $37.00 discounted price Can$29.95
Saxx
Black boxer brief
DROPTEMP™ regular price $37.00 discounted price Can$29.95
Saxx
Neutral boxer briefs
DROPTEMP™ - 3-pack discounted price Can$100.00
Saxx

Editor's pick

Red boxer brief
DROPTEMP™ discounted price Can$37.00
Saxx
Brown boxer brief
VIBE discounted price Can$37.00
Saxx

New

Winter Skies boxer brief
VIBE discounted price Can$37.00
Saxx
Geo-patterned boxer brief
VIBE discounted price Can$37.00
Saxx

New

Snowmobile yeti boxer brief
VIBE discounted price Can$37.00
Saxx
Heathered-stripe boxer brief
VIBE regular price $37.00 discounted price Can$29.95
Saxx
Animal hockey player boxer brief
VIBE discounted price Can$37.00
Saxx
Bear boxer brief
VIBE discounted price Can$37.00
Saxx
Hot dog boxer brief
VIBE discounted price Can$37.00
Saxx
Off Course boxer brief
VIBE regular price $37.00 discounted price Can$29.95
Saxx
Patchwork desert boxer brief
VIBE regular price $37.00 discounted price Can$29.95
Saxx
Pink leaf boxer briefs
VIBE - 2-pack discounted price Can$67.00
Saxx
Black boxer briefs
VIBE - 2-pack discounted price Can$67.00
Saxx
Wide-stripe boxer briefs
VIBE - 2-pack discounted price Can$67.00
Saxx
Solid boxer briefs
ULTRA - 2-pack discounted price Can$67.00
Saxx
Hockey boxer briefs
VIBE - 2-pack discounted price Can$67.00
Saxx
Pizza and flowers boxer briefs
ULTRA - 2-pack discounted price Can$67.00
Saxx
Gaming boxer brief
ULTRA discounted price Can$37.00
Saxx
Pixelated football boxer brief
ULTRA discounted price Can$37.00
Saxx

New

Snow Days boxer brief
ULTRA discounted price Can$37.00
Saxx
Rugby stripe boxer brief
ULTRA discounted price Can$37.00
Saxx
Solid light boxer brief
ULTRA discounted price Can$37.00
Saxx
Graphic-stripe boxer brief
KINETIC HD discounted price Can$40.00
Saxx
Piping micro-mesh boxer brief
KINETIC HD discounted price Can$40.00
Saxx
Wild animal micro dotwork boxer brief
QUEST discounted price Can$38.00
Saxx
Colourful band pure cotton boxer briefs
5-pack discounted price Can$82.00
Calvin Klein
Classic stretch cotton boxer briefs
3-pack discounted price Can$54.00
Calvin Klein
Classic microfibre boxer briefs
3-pack discounted price Can$60.00
Calvin Klein
Modern Cotton Stretch boxer briefs
3-pack regular price $54.00 discounted price Can$39.95
Calvin Klein
Stretch cotton solid boxer briefs
3-pack regular price $54.00 discounted price Can$39.95
Calvin Klein
Classic boxer briefs
3-pack discounted price Can$54.00
Calvin Klein
Solid classic boxer briefs
5-pack discounted price Can$82.00
Calvin Klein
Cotton Stretch boxer briefs
3-pack discounted price Can$54.00
Calvin Klein
Microfiber Stretch boxer briefs
3-pack discounted price Can$60.00
Calvin Klein
Reprocessed modal boxer briefs
3-pack regular price $84.00 discounted price Can$59.95
Calvin Klein
Soft shade pure cotton boxer briefs
3-pack discounted price Can$54.00
Calvin Klein
Logo-band stretch cotton boxer briefs
3-pack regular price $54.00 discounted price Can$39.95
Calvin Klein
Reconsidered Steel silver-waist boxer briefs
3-pack discounted price Can$74.00
Calvin Klein
Reconsidered Steel logo-waist boxer briefs
3-pack discounted price Can$74.00
Calvin Klein
Solid modal boxer brief regular price $19.99 discounted price Can$9.99
Calvin Klein
Solid logo boxer brief regular price $20.00 discounted price Can$15.99
Calvin Klein

New

Essential Micro blue boxer brief regular price $25.00 discounted price Can$19.99
Nike
Dri-FIT Essential Micro multicolour boxer briefs
3-pack discounted price Can$58.00
Nike
Essential Cotton Stretch boxer briefs
3-pack discounted price Can$52.00
Nike
Dri-FIT Everyday pop band boxer briefs
3-pack discounted price Can$52.00
Nike
Dri-FIT ReLuxe heathered-waist boxer briefs
2-pack regular price $52.00 discounted price Can$39.95
Nike
Dri-FIT ADV Micro boxer briefs
3-pack regular price $64.00 discounted price Can$39.95
Nike
Dri-FIT Essential Micro graphic boxer briefs
3-pack discounted price Can$58.00
Nike
Dri-FIT Essential Micro multicolour boxer briefs
3-pack discounted price Can$58.00
Nike
Colourful Dri-FIT ReLuxe boxer briefs
2-pack regular price $52.00 discounted price Can$39.95
Nike
Embroidered logo loose poplin trunk regular price $32.00 discounted price Can$19.99
Polo Ralph Lauren
Embroidered logo loose poplin trunk regular price $32.00 discounted price Can$19.99
Polo Ralph Lauren
Embroidered logo loose poplin trunk regular price $32.00 discounted price Can$19.99
Polo Ralph Lauren

New

Logo waist solid trunk discounted price Can$45.00
Ron Dorff
Pure cotton boxer brief
3-pack discounted price Can$50.00
Tommy Hilfiger
Logo boxer briefs
3-pack discounted price Can$50.00
Tommy Hilfiger

Editor's pick

Preppy-pattern poplin boxer brief regular price $25.00 discounted price Can$19.99
Tommy Hilfiger
Mini-check poplin boxer brief regular price $25.00 discounted price Can$19.99
Tommy Hilfiger
Colourful waist boxer brief regular price $30.00 discounted price Can$19.99
Paul Smith
Lightning bolt boxer brief regular price $20.00 discounted price Can$15.99
Undz
Kitten boxer brief discounted price Can$20.00
Undz
Donkeyz boxer brief discounted price Can$20.00
Undz
Ducks boxer brief regular price $20.00 discounted price Can$15.99
Undz
Cake boxer brief discounted price Can$20.00
Undz
Ice cream sandwich boxer brief discounted price Can$20.00
Undz
Flower Power boxer brief discounted price Can$20.00
Undz
Intergalactic cats boxer brief discounted price Can$20.00
Undz
Outrun boxer brief discounted price Can$20.00
Undz
Hippies boxer brief discounted price Can$20.00
Undz
Sundae boxer brief regular price $20.00 discounted price Can$15.99
Undz
Mushroom boxer brief regular price $36.00 discounted price Can$24.95
BN3TH
Vibrant palm tree boxer brief regular price $36.00 discounted price Can$24.95
BN3TH
Mountain camping boxer brief discounted price Can$36.00
BN3TH
Buenos Dias boxer brief regular price $36.00 discounted price Can$24.95
BN3TH

New

Mixed stripe boxer brief discounted price Can$36.00
BN3TH

New

Block-stripe boxer brief discounted price Can$36.00
BN3TH

New

Cyan stripe boxer brief discounted price Can$30.00
BN3TH
Floral and solid boxer briefs
2-pack discounted price Can$64.00
BN3TH
Solid and camouflage boxer briefs
2-pack regular price $64.00 discounted price Can$49.95
BN3TH
Micro-dotwork solid boxer brief discounted price Can$20.00
3 for $39.95
Pair of Thieves
Micro-dotwork patterned boxer brief discounted price Can$20.00
3 for $39.95
Pair of Thieves
Flag of the United States

Are you in the United States?

Visit simons.com