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Playboy

Shop the latest collections available at Side Step Online. Free delivery for orders over R500.00. Easily find your nearest Side Step store.
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Playboy is more than just a mere clothing brand, it’s a movement that has inspired individuals for over 69 years. With a touch of alluring mystery, Playboy Considers fashion as a form of expression, their significant collection of unisex apparel and accessories seeks to empower you to embrace your confidence and free you from the ordinary. The Brand Shatters barriers and questions the status quo. They don't shy away from sparking debate, and their clothing reflects the same prominence. Whether you're open-minded, body-positive, or simply value equality and the finer things in life, Playboy offers a space to express yourself authentically. ...

At Side-Step, we are proud to offer a curated selection of Playboy apparel and accessories. Explore their collection and discover the confidence to break boundaries and express your unique style. We offer a variety of sizes and styles to ensure you find the perfect fit. Embrace the Playboy lifestyle and embark on a journey of self-discovery. Shop our collection of Playboy apparel and accessories online or visit a Side-Step store near you.

  • PYB383MU-PYB-WERNSTERN-3PK-MULTI-PB-AW26-MC-0064-V1
    Playboy 3 Pack Western Trunks Mens Multi
    R 299.99
    Playboy 3 Pack Western Trunks Mens Multi
  • PYB376LN-PYB-PERSUE-WINDBRKR-NIGHT-PB-AW24-MA-0006-V1
    Playboy Persue Pleasure Windbreaker Mens Night
    R 749.99
    Playboy Persue Pleasure Windbreaker Mens Night
  • PYB369B-PYB-BRAVE-CARGO-BLK-PB--AW26-MB-0040-V1
    Playboy Brave And Bold Cargo Pants Mens Black
    R 749.99
    Playboy Brave And Bold Cargo Pants Mens Black
  • PYB367BG-PYB-PINSTRIP-PLEASURE-BLUGRY--PB-AW26-MB-0045-V1
    Playboy Pinstripe Pleasure Trackpants Mens Blue/Grey
    R 599.99
    Playboy Pinstripe Pleasure Trackpants Mens Blue/Grey
  • PYB351B-PYB-SKETCHED-KISS-BLK-PB-AW26-MA-0035-V1
    Playboy Sketched Kiss T-Shirt Mens Black
    R 349.99
    Playboy Sketched Kiss T-Shirt Mens Black
  • PYB340W-PYB-BULL-RIDING-TSHT-WHT-PB-AW26-MA-0023-V1
    Playboy Bull Riding Bunny T-Shirt Mens White
    R 349.99
    Playboy Bull Riding Bunny T-Shirt Mens White
  • PYB337CH-PB-WILD-WEST-CHARCHOAL-PB-AW26-MA-0019-V1
    Playboy Wild West T-Shirt Mens Charcoal
    R 499.99
    Playboy Wild West T-Shirt Mens Charcoal
  • PYB317SU-PYB-INFLATABLE-SUMMER-PB-SS25-MB-0005-V1
    Playboy Inflatable RPT Swimshorts Mens Summer
    R 399.99
  • PYB308DG-PB-CARGO-DRKGRN-PB-SS25-MB-0059-V1
    Playboy Essential Cargo Pants Mens Dark Green
    R 849.99
  • PYB271B-PB-CHERRIES-BLK-PB-SS25-MA-0038-V1
    Playboy Playful Cherries T-Shirt Mens Black
    R 449.99
  • PYB293DT-PYB-OLD-ENGLISH-DP-TLEAL-PB-SS25-MA-0071-V1
    Playboy Old English T-Shirt Mens Teal
    R 399.99
  • PYB281W-PLAYBOY-INFLATABLE-WHT-PB-SS25-MA-003-V1
    Playboy Inflatable T-Shirt Mens White
    R 399.99
  • PYB284WS-PLAYBOY-FINDING-WHTSND-PBSS25-MA-0009-V1
    Playboy Finding Paradise T-Shirt Mens White Sand
    R 399.99
  • PYB315TP-PYB-WOODCUT-TROPCL-PB-SS24-MB-0004-V1
    Playboy Woodcut Swimshorts Mens Tropical
    R 399.99
  • PYB315I-PLAYBOY-WOODCUT-SWIM-INDIGO-PB-SS25-0004-V1
    Playboy Woodcut Swimshorts Mens Indigo
    R 399.99
  • PYB306B-PLAYBOY-HAWAII-BUNNY-CRGO-BLK-PB-SS25-MB-0013-V1
    Playboy Hawaii Bunny Cargo Pants Mens Black
    R 899.99
  • PYB288B-PB-LOCKUP-WSHDBK-PB-SS25-MA-0064-V1
    Playboy Vertical Lockup Acid T-Shirt Mens Washed Black
    R 549.99
  • PYB286B-PYB-HAWAII-BUNNY-BLK-PB-SS25-0014-V1
    Playboy Hawaii Bunny T-Shirt Mens Black
    R 449.99
  • PYB332B-PYB-SLING-BLK-PB-SS25-0090-V1
    Playboy Sling Bag Black
    R 249.99
  • PYB334WI-PB-SOCK-WHT-INDIGO-PBSS25-MC-0086-V1
    Playboy Socks White/Indigo
    R 199.99

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Iconic Style, Modern Edge: The Playboy Collection at Side-Step

More than just a brand, Playboy is a global symbol of rebellion, style, and empowerment. At Side-Step, we bring you a curated collection of this legendary brand's most celebrated apparel and accessories. With its iconic Bunny logo, Playboy offers a bold and playful aesthetic that’s as relevant today as it was in the '50s.

Streetwear & Nostalgia

Explore comfortable tracksuits, oversized hoodies, and bold graphic tees that are perfect for both sport and street style. Our Playboy collection also features a variety of accessories, including caps and bags. Whether you're a devoted fan of nostalgia or a newcomer to the brand, our collection has something for every style, ensuring you can rock a timeless look with confidence.

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