• Underwear - masculine underwear & loungewear

    Men's Underwear

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    3 for $34.95

    Striped microfibre trunk US$19.00
    3 for $34.95
    Le 31
    Recycled nylon dotted trunk US$19.00
    3 for $34.95
    Le 31
    Microfibre jacquard trunk US$19.00
    3 for $34.95
    Le 31
    Aqua jacquard trunk US$19.00
    3 for $34.95
    Le 31

    New

    Recycled microknit brief US$19.00
    3 for $34.95
    Le 31
    Recycled micro nylon brief US$19.00
    3 for $34.95
    Le 31
    Micro nylon dotwork brief US$19.00
    3 for $34.95
    Le 31
    Aqua jacquard brief US$19.00
    3 for $34.95
    Le 31
    Trimmed houndstooth brief US$19.00
    3 for $34.95
    Le 31
    Jacquard microfibre brief US$19.00
    3 for $34.95
    Le 31
    Striped microfibre brief US$19.00
    3 for $34.95
    Le 31

    Most popular trunks

    Most popular boxer briefs

    Most popular briefs

    Essential microfibre brief US$35.00
    Calvin Klein
    NFL jockstrap US$25.00
    Pump!

    Most popular multi-packs

    Most popular tanks & T-shirts

    Trunks

    Leopard trunk US$19.00
    Le 31

    Editor's pick

    Slim fit trunk US$30.00
    JM

    Editor's pick

    Solid bamboo rayon trunk $30.00 US$19.99
    Bamboo Underwear

    Editor's pick

    Solid bamboo rayon trunk $30.00 US$19.99
    Bamboo Underwear
    Signature waist trunk US$19.00
    Jack & Jones
    Signature waist trunk US$19.00
    Jack & Jones
    Logo waist trunk US$19.00
    Jack & Jones
    Pop foliage trunk US$19.00
    Jack & Jones
    Geo lettering trunk US$19.00
    Jack & Jones
    Optical dot trunk US$19.00
    Jack & Jones
    Optical dot trunk US$19.00
    Jack & Jones
    CK1 multi-logo trunk US$20.00
    Calvin Klein
    Modal trunk US$30.00
    Calvin Klein
    Essential microfibre trunk US$35.00
    Calvin Klein

    New

    Solid croc trunk US$20.00
    Lacoste

    New

    Solid croc trunk US$20.00
    Lacoste

    New

    Solid croc trunk US$20.00
    Lacoste

    New

    Dress up puppies trunk US$30.00
    Paul Smith

    New

    Pop Art trunk US$30.00
    Paul Smith

    New

    Balloon signs trunk US$30.00
    Paul Smith

    New

    Pop stripe trunk US$30.00
    Paul Smith

    New

    Alphabet confetti trunk US$30.00
    Paul Smith
    Retro stripe boxer brief US$30.00
    Paul Smith

    New

    Teal stripe trunk US$30.00
    Paul Smith
    Ardent flower boxer brief $30.00 US$14.99
    Paul Smith

    New

    Iconic trunk
    3-pack
    US$50.00
    Lacoste
    Croc trunk
    3-pack
    US$45.00
    Lacoste
    CK1 trunk
    3-pack
    US$50.00
    Calvin Klein
    Metallic trunk
    3-pack
    US$55.00
    Calvin Klein

    Boxer briefs

    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!

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