Free Shipping on orders $40+ within the US

Chill Time Rewards: Earn & Redeem Points on All Purchases

11 products

Print Collection - Limited Edition

Boxer briefs crafted from a blend of ridiculously soft, breathable fabrics, our Performance Boxer Briefs are designed to keep you cool, dry, and comfortable all day. The moisture-wicking technology draws sweat away from your skin while the stretchy fabric moves with you for ultimate freedom of movement.

PERFORMANCE BOXERS

Made using a blend of breathable micro-mesh polyamide nylon and spandex. A silky soft feel, like your favorite golf shirt. Cool, soft, breathable and very quick drying. Chill Boys Performance Boxers are perfect underwear for hiking, traveling, sleeping or an active day of work and play.

  • Chill Boys Performance Boxers - Cool, Soft, Breathable Men's wicking Underwear - Gray

    Grey
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Grey
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Performance Boxers - Cool, Soft, Breathable Men's wicking Underwear - Black

    Black
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Black
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Performance Boxers - Cool, Soft, Breathable Men's wicking Underwear - Blue

    Blue
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Blue
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • The caddie golf boxers chill boys boxers for golf

    Green - Golf
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Green - Golf
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys pickleball boxers boxer shorts for pickleball

    Blue-Pickleball
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Blue-Pickleball
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • White performance boxers white mens underwear

    Glacial White
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Glacial White
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Performance Boxers - Cool, Soft, Breathable Men's Boxers

    Navy-Tackle Box
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    BEST SELLER

    Navy-Tackle Box
    Made using a blend of soft, breathable micro-mesh polyamide nylon and spandex.

    (751)
    $29.95
    $28.00 $29.95
    BEST SELLER

BAMBOO BOXERS

Made using super soft bamboo fabric and a blend of spandex for added stretch and flex. Chill Boys Bamboo Boxers are the ultimate for soft relaxing comfort! The breathable bamboo fabric is naturally cool, soft and fights odors. In addition to just being super sweet boxers, they are also eco-friendly! Bamboo is one of the fastest-growing plants on the planet so you can feel good about feeling good.

  • Chill Boys Soft Bamboo Boxers - Plush Luxury Men's Boxer Shorts - Black

    Black
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Black
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Soft Bamboo Boxers - Plush Luxury Men's Boxer Shorts - Cool Blue

    Cool Blue
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Cool Blue
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Soft Bamboo Boxers - Plush Luxury Men's Boxer Shorts - Gray

    Grey
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Grey
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Chill Boys Soft Bamboo Boxers - Plush Luxury Men's Boxer Shorts - Red

    Red
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Red
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • purple boxers chill boys bamboo boxers vikings purple

    Purple
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Purple
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER
  • Navy blue boxers navy blue mens underwear

    Navy Blue
    Soft bamboo fabric blended with spandex for added stretch and flex

    BEST SELLER

    Navy Blue
    Soft bamboo fabric blended with spandex for added stretch and flex

    (1,054)
    $29.95
    $28.00 $29.95
    BEST SELLER

BAMBOO BOXER BRIEFS

Made using our super soft bamboo fabric, but with a fun added feature. We use advanced micro-mesh fabric in the inner-thigh to create a no-friction glide zone. No chaffing and very breathable. Soft bamboo fabric is cooler than cotton boxers and offers amazing stretch. Our bamboo viscose fabric is naturally anti-microbial keeping you fresh and odor-free. You will also feel great with the comfy support pouch and easy access fly. The no-sweat vent in the lower back area will keep you cool and dry. Ahh, so chill :)

  • Soft Bamboo Boxer Briefs with Anti-Chafing Glide Zone - Bamboo Black

    Bamboo Black
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Bamboo Black
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING
  • Soft Bamboo Boxer Briefs with Anti-Chafing Glide Zone - Bamboo Green

    Bamboo Green
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Bamboo Green
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING
  • grey boxer briefs chill boys bamboo underwear

    Bamboo Gray
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Bamboo Gray
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING
  • purple boxer briefs men's underwear chill boys boxers

    Vikings Purple
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Vikings Purple
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING
  • white bamboo boxer briefs white mens unerwear

    Glacier White
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Glacier White
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING
  • Navy Blue Boxer Briefs Navy Blue mens underwear

    Navy Blue
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    ANTI-CHAFING

    Navy Blue
    Soft, stretchy bamboo fabric with micro-mesh fabric to provide a no-friction glide zone

    (281)
    $32.95
    $32.00 $32.95
    ANTI-CHAFING

PERFORMANCE TRUNKS

Made using our high-performance micro-mesh fabric, our Performance Trunks feature quick-drying, moisture-wicking comfort. Chill Boys Trunks are also soft and super stretchy so they move when you move. Trunks are shorter than boxer briefs and have an athletic fit featuring a comfortable pouch support. Our moisture-wicking fabric is quick drying, giving you odor eliminating confidence!

  • Onyx Black - Chill Boys Soft Stretch, Quick-Dry Trunks - angle view

    Onyx Black
    Quick-drying, moisture-wicking trunks with athletic fit and comfortable pouch support

    STRETCHY

    Onyx Black
    Quick-drying, moisture-wicking trunks with athletic fit and comfortable pouch support

    (64)
    $29.95
    $29.95
    STRETCHY

Chill Boys Boxers

Five amazing styles of our famously cool, soft, and comfy men's boxers and boxer briefs. You'll love the fit, feel, and comfort of our bamboo underwear and performance boxers - no matter your style!