Men's Pants & Shorts

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Black men's sweat shorts with white rabbit head logo, drawstring waist, flat lay
Playboy Men's Rabbit Head Sweat Shorts
$38.40 $64.00
Navy tie-dye sweatshorts with earth, butterfly, and bold PLAYBOY graphic on the leg.
Playboy Tie-Dye Au Naturel Sweatshorts
$34.20 $57.00
Men's cream sweatpants with Playboy Bunny graphics and black text on left leg and thigh.
Playboy Men's Bank Roll Sweatpants
$52.20 $87.00
Men's black sweatpants with pink Playboy text and neon bunny outline graphic
Playboy Men's Bunny Outline Sweatpants
$52.20 $87.00
Men's grey sweat shorts with black bunny graphics and PLAYBOY text on both legs
Playboy Men's Double Bunny Sweat Shorts
$34.80 $58.00
Yellow sweatpants with red aviation wings logo, elastic waistband and cuffs, flat lay.
Playboy Aviation Wings Sweatpants
$120.60 $201.00
Beige sweatpants with vintage magazine cover graphic and red 'PLAYBOY' text on leg
Playboy December 1966 Cover Sweatpants
$45.00 $75.00
Black sweatpants with anime-style pinup girl graphics, red rabbit logo, and Japanese text
Playboy Tokyo Club Covergirl Sweatpants
$48.60 $81.00
Black sweatpants with colorful Tokyo-style side graphic and cherry logo on the hip
Playboy Tokyo Club 3.0 Sweatpants
$48.60 $81.00
Male model wearing black lace boxer briefs against light background
Playboy Men's Lace Boxer Brief
$18.00 $30.00
Male model wearing charcoal ribbed men's trunk underwear with black waistband on white background
Playboy Men's Essentials Rib Trunk
$19.80 $33.00
Man wearing black velour track pants and matching jacket with white piping details
Playboy Men's Velour Pant
$55.20 $92.00
Male model in black harness and briefs set with heart detail and pink Playboy logo trim
Playboy Men's Broken Hearts Harness
$12.60 $21.00
Black men's sweatpants with colorful 'Playboy' logo on left leg, elastic waistband, and drawstring.
Playboy Men's Amenities Sweatpants
$34.80 $58.00
Black sweatpants with green camo PLAYBOY text graphic on right leg, elastic waist and cuffs
Playboy Hare Green Camo Sweatpants
$45.00 $75.00
Burgundy sweatpants with December 1970 magazine cover print and PLAYBOY text graphic.
Playboy December 1970 Cover Sweatpants
$45.00 $75.00
Olive green sweatpants with drawstring waist and small black bunny logo on left pocket.
Playboy Bunny Basics Sweatpants
$52.20 $87.00
Man modeling white boxer briefs with red rabbit head pattern and red waistband with visible logo
Playboy Rabbit Head Boxer Briefs
$18.00 $30.00
Dark green athletic shorts with white bunny logo, number 53, and side stripes
Playboy 1953 Sport Shorts
$38.40 $64.00
Yellow sweatpants with aviation-inspired graphics and side logo, elastic waistband and cuffs.
Playboy Aviation Wings N950PB Sweatpants
$102.60 $171.00
Navy blue men's sweatshorts with drawstring waist and white bunny logo on left leg
Playboy Bunny Basics Sweatshort
$38.40 $64.00
Men's neon yellow beach shorts with drawstring waist and graphic palm tree logo
Playboy Men's Beach Club Graphic Shorts
$30.00 $50.00
Red men's classic mesh basketball shorts with elastic waistband and PLAYBOY logo
Playboy Men's Classic Basketball Shorts
$34.80 $58.00
Men's classic brown trousers with pleats and embroidered bunny logo on pocket, front view
Playboy Men's Classic Trouser
$68.40 $114.00
Two-pack men's boxer briefs, one green, one red and white with logo waistband.
Playboy Men's Essential Underwear 2-Pack
$26.40 $44.00
Male model wearing orange men's modal briefs with branded waistband, front view
Playboy Men's Essentials Modal Brief
$17.40 $29.00
Man modeling orange modal trunk underwear with white waistband and logo on plain background
Playboy Men's Essentials Modal Trunk
$18.00 $30.00
Men's basketball shorts with wavy blue and white checker pattern and elastic waistband
Playboy Men's Wavy Checker Basketball Shorts
$34.20 $57.00
White sweatpants with black drawstring and black bunny logo on left upper thigh
Playboy x John Richmond Classic Logo Sweatpants
$61.60 $154.00
Brown sweatpants with yellow rabbit head pattern and Richmond text graphic on leg
Playboy x John Richmond Repeating Rabbit Head Sweatpants
$56.00 $140.00
Black mesh shorts with white checkered side panels and subtle logo accents
Playboy Speed Racer Mesh Shorts
$38.40 $64.00
Smiling man modeling collage-print boxer briefs with playful graphic pattern on white background
The Playboy Cover Collage Boxer Brief
$18.00 $30.00
Shirtless male model wearing orange Playboy-themed boxer briefs with vintage magazine cover print
The Playboy October 1966 Cover Boxer Brief
$16.20 $27.00
Men's boxer briefs with colorful vintage magazine cover print and PLAYBOY logo waistband
The Playboy March 1975 Cover Boxer Brief
$18.00 $30.00
Male model in red boxer briefs with PLAYBOY logo waistband and letter P graphic on front
Playboy Boxer Brief
$12.60 $21.00
Navy blue lounge shorts with red repeating rabbit head pattern, elastic waistband, side pockets
Playboy Repeating Rabbit Head Lounge Shorts
From $31.20 $52.00
Navy jogger pants with yellow PLAYBOY text and vintage magazine cover graphic on the leg
Playboy March 1968 Cover Jogger
$52.20 $87.00
Black sweatpants with color block lettering on the leg and a white bunny graphic on the thigh
Playboy Color-Block Sweatpants
$51.60 $86.00
Black sweat shorts with white bunny logo and number 53 graphic on the front
Playboy 1953 Sweatshorts
$34.80 $58.00
Light grey sweatshorts with red rabbit head logo and blue Japanese text on front
Playboy Japanese Rabbit Head Sweatshorts
$34.20 $57.00
Navy blue men's golf shorts with white bunny logo on left leg, flat lay view
Playboy Puma Golf Shorts
$58.80 $98.00
Brown crocodile-embossed faux leather flare pants with elastic waistband, flat lay
Playboy Crocodile Leather Flare Pant
$170.40 $284.00
Colorful pants featuring repeated 1970 magazine cover graphic print with peace sign woman
Playboy x Soulland September 1970 Playboy Cover Pants
$113.60 $284.00
Light purple faux leather flare pants with elastic waistband and front pockets, laid flat
Playboy Leather Flare Pants
$139.80 $233.00
Shorts with American flag pattern on a white background
Playboy Fourth of July Swim Trunk
$34.80 $58.00
Gray shorts with a green logo on a white background
Playboy Men's 15" Core Swim Trunks
$28.80 $48.00
Boxer briefs with Playboy and dollar bill design on a white background
Playboy x PSD Bet Brief
$28.00