Simons Men Underwear & Loungewear

Boxers & Briefs

Men's Underwear

Trunks
Trunks
Boxer Briefs
Boxer Briefs
Multi-Packs
Multi-Packs
Briefs
Briefs
Performance Underwear
Performance Underwear

Featured

  • Le 31 Patterned Blue Blue pinstripe trunk for men

    Le 31

    Blue pinstripe trunk

    Can$20.00

    3 for $39.95

  • Le 31 Patterned Grey Mini diamond trunk for men

    Le 31

    Mini diamond trunk

    Can$20.00

    3 for $39.95

  • Le 31 Patterned Grey Scale-look trunk for men

    Le 31

    Scale-look trunk

    Can$20.00

    3 for $39.95

Featured

  • Le 31 Patterned Blue Blue pinstripe brief for men

    Le 31

    Blue pinstripe brief

    Can$20.00

    3 for $39.95

  • Le 31 Patterned Grey Mini diamond brief for men

    Le 31

    Mini diamond brief

    Can$20.00

    3 for $39.95

  • Le 31 Patterned Grey Scale-look brief for men

    Le 31

    Scale-look brief

    Can$20.00

    3 for $39.95

  • Le 31 Marine Blue Solid viscose trunk for men
    Le 31 Marine Blue Solid viscose trunk for men
    Le 31 Marine Blue Solid viscose trunk for men
    Le 31 Marine Blue Solid viscose trunk for men

    Le 31

    Solid viscose trunk

    Can$20.00

  • Le 31 Orange Solid viscose trunk for men
    Le 31 Orange Solid viscose trunk for men
    Le 31 Orange Solid viscose trunk for men
    Le 31 Orange Solid viscose trunk for men

    Le 31

    Solid viscose trunk

    Can$20.00

  • Le 31 Bottle Green Solid viscose trunk for men
    Le 31 Bottle Green Solid viscose trunk for men
    Le 31 Bottle Green Solid viscose trunk for men
    Le 31 Bottle Green Solid viscose trunk for men

    Le 31

    Solid viscose trunk

    Can$20.00

  • Le 31 Patterned Black Contrasting topstitch trunk for men
    Le 31 Patterned Black Contrasting topstitch trunk for men
    Le 31 Patterned Black Contrasting topstitch trunk for men
    Le 31 Patterned Black Contrasting topstitch trunk for men
    Le 31 Patterned Black Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

  • Le 31 Brown Contrasting topstitch trunk for men
    Le 31 Brown Contrasting topstitch trunk for men
    Le 31 Brown Contrasting topstitch trunk for men
    Le 31 Brown Contrasting topstitch trunk for men
    Le 31 Brown Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

  • Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

  • New

    Saxx Patterned Blue Colourful illustration boxer brief DAYTRIPPER for men

    Saxx

    Colourful illustration boxer brief
    DAYTRIPPER

    Can$29.00

  • Le 31 Assorted navy Mixed stripe viscose trunk for men

    Le 31

    Mixed stripe viscose trunk

    Can$25.00

  • Editor's pick

    Le 31 Assorted navy Favourite snacks trunk for men
    Le 31 Assorted navy Favourite snacks trunk for men
    Le 31 Assorted navy Favourite snacks trunk for men
    Le 31 Assorted navy Favourite snacks trunk for men

    Le 31

    Favourite snacks trunk

    $20.00 Can$15.99

  • Calvin Klein White Classic crew-neck T-shirts 3-pack for men
    Calvin Klein White Classic crew-neck T-shirts 3-pack for men

    Calvin Klein

    Classic crew-neck T-shirts
    3-pack

    Can$54.00

  • New

    Le 31 White Stretch cotton briefs 3-pack for men
    Le 31 White Stretch cotton briefs 3-pack for men

    Le 31

    Stretch cotton briefs
    3-pack

    Can$29.95

  • Saxx Black Solid micro-mesh boxer briefs SPORT MESH - 2-pack for men
    Saxx Black Solid micro-mesh boxer briefs SPORT MESH - 2-pack for men

    Saxx

    Solid micro-mesh boxer briefs
    SPORT MESH - 2-pack

    Can$50.00

  • Le 31 Slate Blue Contrasting topstitch trunk for men
    Le 31 Slate Blue Contrasting topstitch trunk for men
    Le 31 Slate Blue Contrasting topstitch trunk for men
    Le 31 Slate Blue Contrasting topstitch trunk for men
    Le 31 Slate Blue Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

  • Le 31 Sapphire Blue Contrasting topstitch trunk for men
    Le 31 Sapphire Blue Contrasting topstitch trunk for men
    Le 31 Sapphire Blue Contrasting topstitch trunk for men
    Le 31 Sapphire Blue Contrasting topstitch trunk for men
    Le 31 Sapphire Blue Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

  • Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men
    Le 31 Patterned Blue Contrasting topstitch trunk for men

    Le 31

    Contrasting topstitch trunk

    Can$15.00

    3 for $34.95

Multi-packs

  • Le 31 Patterned Blue Colourful organic cotton and modal boxer briefs 3-pack for men
    Le 31 Patterned Blue Colourful organic cotton and modal boxer briefs 3-pack for men

    Le 31

    Colourful organic cotton and modal boxer briefs
    3-pack

    $45.00 Can$29.95

  • Le 31 Patterned Green Colourful organic cotton and modal boxer briefs 3-pack for men
    Le 31 Patterned Green Colourful organic cotton and modal boxer briefs 3-pack for men

    Le 31

    Colourful organic cotton and modal boxer briefs
    3-pack

    $45.00 Can$29.95

  • Le 31 Teal Solid and printed trunks 2-pack for men
    Le 31 Teal Solid and printed trunks 2-pack for men
    Le 31 Teal Solid and printed trunks 2-pack for men
    Le 31 Teal Solid and printed trunks 2-pack for men
    Le 31 Teal Solid and printed trunks 2-pack for men

    Le 31

    Solid and printed trunks
    2-pack

    $35.00 Can$24.95

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Men's Boxers & Briefs

Whether you're working, training at the gym, or simply relaxing at home, comfort is a priority. And when it comes to comfort, choosing the right underwear is key. At Simons, we offer a wide variety of trunks, boxers, and boxer briefs to suit your every need.

 

Take your pick in our selection of high-quality, comfortable, and sometimes playful designs by Calvin Klein, Jack & Jones, BOSS by HUGO BOSS, SAXX, or our private brand, Le 31. Make sure to choose the fabric that's right for you. Your underwear should be stretchy and breathable. Cotton, modal, and bamboo rayon are particularly popular!