Login

Cart

Your cart is empty

Signup for our newsletter

Sign up for and get exclusive offers, VIP access, and the spiciest updates. Don’t miss out!

Men's Pants & Shorts

Sort by

56 products

Filters
Men's Rabbit Head Sweat Shorts - PlayboyMen's Rabbit Head Sweat Shorts - Playboy
Men's Rabbit Head Sweat Shorts Sale price$58.00
Color
Tie - Dye Au Naturel Sweatshorts - PlayboyTie - Dye Au Naturel Sweatshorts - Playboy
Tie-Dye Au Naturel Sweatshorts Sale price$51.00
Best Seller
Japanese Rabbit Head Joggers - PlayboyJapanese Rabbit Head Joggers - Playboy
Japanese Rabbit Head Joggers Sale price$73.00
Color
Classic Boxer Brief - PlayboyClassic Boxer Brief - Playboy
Classic Boxer Brief Sale price$21.00
Color
Men's Bank Roll Sweatpants - PlayboyMen's Bank Roll Sweatpants - Playboy
Men's Bank Roll Sweatpants Sale price$79.00
Color
Men's Bunny Outline Sweatpants - PlayboyMen's Bunny Outline Sweatpants - Playboy
Men's Bunny Outline Sweatpants Sale price$79.00
Color
Men's Double Bunny Sweat Shorts - PlayboyMen's Double Bunny Sweat Shorts - Playboy
Men's Double Bunny Sweat Shorts Sale price$52.00
Color
Aviation Wings Sweatpants - PlayboyAviation Wings Sweatpants - Playboy
Aviation Wings Sweatpants Sale price$182.00
Color
December 1966 Cover Sweatpants - PlayboyDecember 1966 Cover Sweatpants - Playboy
December 1966 Cover Sweatpants Sale price$68.00
Tokyo Club Covergirl Sweatpants - Playboy
Tokyo Club Covergirl Sweatpants Sale price$73.00
Tokyo Club 3.0 Sweatpants - Playboy
Tokyo Club 3.0 Sweatpants Sale price$73.00
Men's Lace Boxer Brief - PlayboyMen's Lace Boxer Brief - Playboy
Men's Lace Boxer Brief Sale price$13.50 Regular price$27.00
Color
Men's Essentials Rib Trunk - PlayboyMen's Essentials Rib Trunk - Playboy
Men's Essentials Rib Trunk Sale price$30.00
Color
Best Seller
Men's Velour Pant - PlayboyMen's Velour Pant - Playboy
Men's Velour Pant Sale priceFrom $58.10 Regular price$83.00
Color
Men's Broken Hearts Harness - Playboy
Men's Broken Hearts Harness Sale price$19.00
Color
Men's Broken Hearts Brief Meteorite - PlayboyMen's Broken Hearts Brief Meteorite - Playboy
Men's Broken Hearts Brief Meteorite Sale price$13.50 Regular price$27.00
Color
Best Seller
Men's Broken Hearts Thong Meteorite - PlayboyMen's Broken Hearts Thong Meteorite - Playboy
Men's Broken Hearts Thong Meteorite Sale price$16.00
Color
Men's Amenities Sweatpants - PlayboyMen's Amenities Sweatpants - Playboy
Men's Amenities Sweatpants Sale price$26.00 Regular price$52.00
Color
Hare Green Camo Sweatpants - PlayboyHare Green Camo Sweatpants - Playboy
Hare Green Camo Sweatpants Sale price$34.00 Regular price$68.00
December 1970 Cover Sweatpants - PlayboyDecember 1970 Cover Sweatpants - Playboy
December 1970 Cover Sweatpants Sale price$68.00
Best Seller
Bunny Basics Sweatpants - PlayboyBunny Basics Sweatpants - Playboy
Bunny Basics Sweatpants Sale price$79.00
Color
Rabbit Head Boxer Briefs - PlayboyRabbit Head Boxer Briefs - Playboy
Rabbit Head Boxer Briefs Sale price$13.50 Regular price$27.00
Color
Playboy Mens Champion Boxer - PlayboyPlayboy Mens Champion Boxer - Playboy
Playboy Mens Champion Boxer Sale price$14.50 Regular price$29.00
Color
1953 Sport Shorts - Playboy1953 Sport Shorts - Playboy
1953 Sport Shorts Sale price$58.00
Color
Aviation Wings N950PB Sweatpants - PlayboyAviation Wings N950PB Sweatpants - Playboy
Aviation Wings N950PB Sweatpants Sale price$155.00
Color
Bunny Basics Sweatshort - PlayboyBunny Basics Sweatshort - Playboy
Bunny Basics Sweatshort Sale priceFrom $40.60 Regular price$58.00
Color
Men's Beach Club Graphic Shorts - PlayboyMen's Beach Club Graphic Shorts - Playboy
Men's Beach Club Graphic Shorts Sale price$22.50 Regular price$45.00
Color
Men's Classic Basketball Shorts - PlayboyMen's Classic Basketball Shorts - Playboy
Men's Classic Basketball Shorts Sale price$52.00
Men's Classic Trouser - PlayboyMen's Classic Trouser - Playboy
Men's Classic Trouser Sale price$51.50 Regular price$103.00
Color
Men's Essential Underwear 2 - Pack - PlayboyMen's Essential Underwear 2 - Pack - Playboy
Men's Essential Underwear 2-Pack Sale price$20.00 Regular price$40.00
Color
Men's Essentials Modal Brief - PlayboyMen's Essentials Modal Brief - Playboy
Men's Essentials Modal Brief Sale price$26.00
Color
Men's Essentials Modal Trunk - PlayboyMen's Essentials Modal Trunk - Playboy
Men's Essentials Modal Trunk Sale priceFrom $18.90 Regular price$27.00
Color
Men's Essentials Rib Boxer Brief - PlayboyMen's Essentials Rib Boxer Brief - Playboy
Men's Essentials Rib Boxer Brief Sale price$13.50 Regular price$27.00
Color
Best Seller
Men's Velour Shorts - PlayboyMen's Velour Shorts - Playboy
Men's Velour Shorts Sale price$63.00
Color
Men's Wavy Checker Basketball Shorts - PlayboyMen's Wavy Checker Basketball Shorts - Playboy
Men's Wavy Checker Basketball Shorts Sale price$51.00
Playboy x John Richmond Classic Logo Sweatpants - PlayboyPlayboy x John Richmond Classic Logo Sweatpants - Playboy
Playboy x John Richmond Classic Logo Sweatpants Sale price$140.00
Color
Playboy x John Richmond Repeating Rabbit Head Sweatpants - PlayboyPlayboy x John Richmond Repeating Rabbit Head Sweatpants - Playboy
Playboy x John Richmond Repeating Rabbit Head Sweatpants Sale price$127.00
Color
Playboy x Peaches. Sweatpants - PlayboyPlayboy x Peaches. Sweatpants - Playboy
Playboy x Peaches. Sweatpants Sale price$119.00
Color
Playboy x Pleasures Collide Short - PlayboyPlayboy x Pleasures Collide Short - Playboy
Playboy x Pleasures Collide Short Sale price$83.00
Color
Speed Racer Mesh Shorts - PlayboySpeed Racer Mesh Shorts - Playboy
Speed Racer Mesh Shorts Sale price$58.00
Tennis Club Shorts - PlayboyTennis Club Shorts - Playboy
Tennis Club Shorts Sale price$58.00
Color
The October 1966 Cover Boxer Brief - PlayboyThe October 1966 Cover Boxer Brief - Playboy
The October 1966 Cover Boxer Brief Sale price$12.00 Regular price$24.00
The Cover Collage Boxer Brief - PlayboyThe Cover Collage Boxer Brief - Playboy
The Cover Collage Boxer Brief Sale price$13.50 Regular price$27.00
The March 1975 Cover Boxer Brief - PlayboyThe March 1975 Cover Boxer Brief - Playboy
The March 1975 Cover Boxer Brief Sale price$27.00
Color
Boxer Brief - PlayboyBoxer Brief - Playboy
Boxer Brief Sale price$9.50 Regular price$19.00
Color
Repeating Rabbit Head Lounge Shorts - PlayboyRepeating Rabbit Head Lounge Shorts - Playboy
Repeating Rabbit Head Lounge Shorts Sale price$52.00
Color
March 1968 Cover Jogger - PlayboyMarch 1968 Cover Jogger - Playboy
March 1968 Cover Jogger Sale price$79.00
Men's Broken Hearts Jock Strap Meteorite - PlayboyMen's Broken Hearts Jock Strap Meteorite - Playboy
Men's Broken Hearts Jock Strap Meteorite Sale price$19.00
Color