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Loose Fit & Baggy Shorts

S/DOUBLE Gentleman Walkshort Charcoal

$110.00
S/DOUBLE Denim Standard Short One Wash

$110.00
S/DOUBLE Denim Standard Short Black Wash

$110.00
Carhartt WIP Cotton Trunks Grey Heather

$70.00
Pass~Port Herringbone Leagues Club Shorts Olive

$130.00
Hoddle Bermuda Jersey Short Navy

$130.00
Hoddle Bermuda Jersey Short Grey

$130.00
Dickies DX200 Lightweight Canvas 11" Relaxed Fit Carpenter Short Dark Indigo

$100.00
Dickies 17293 10" 5 Pocket Regular Fit Short Light Indigo

$110.00
Cash Only Logo Denim Shorts Washed Black

$110.00
Crawling Death TV Skull Mesh Shorts

$119.00
Crawling Death Reaper Camo Shorts

$139.00
Crawling Death Web Denim Shorts Washed Black

$129.00
Hoddle Bermuda Short Tan

$130.00
Xlarge Denim Work Short Pepper

$100.00
Pass~Port Workers Club Jean Short Faded Wash Black

$130.00
Pass~Port Workers Club Jean Short Faded Wash Dark Indigo

$130.00
Pass~Port Workers Club Jean Short R43 Washed Black

$130.00
Butter Goods Spider Denim Shorts Dark Indigo

$120.00
Butter Goods Bark Camo Denim Shorts Black

$130.00
Butter Goods Spider Denim Shorts Acid Brown

$120.00
Gramicci G-Shorts Black

$140.00
Gramicci G-Shorts Olive

$140.00
Service Works Classic Canvas Chef Shorts Black

$130.00
Brick + Mortar x Dizdain Baggy Track Shorts Washed Black

$60.00
Crawling Death Web Denim Shorts Acid Black

$130.00
Xlarge Bull Denim 91 Short Vintage Blue

$100.00
Xlarge Bull Denim 91 Short Olive Grey

$100.00
Xlarge Bull Denim 91 Short Dirty Blue

$100.00
Butter Goods Weathergear Heavy Weight Denim Shorts Worn Indigo

$110.00
Butter Goods Work Shorts Digital Camo

$130.00
Butter Goods Field Cargo Shorts Washed Rust

$120.00

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Loose Fit & Baggy Shorts

Baggy shorts rose from the rubble of '90s skateboarding and hip-hop culture, when comfort and mobility trumped the skin-tight trends of previous decades. What began as a practical choice for athletes and street skaters evolved into a defining aesthetic that's cycled through mainstream acceptance, ironic rejection, and triumphant revival over three decades.

By the mid-2000s, the pendulum had swung dramatically toward slim silhouettes, pushing baggy shorts into the realm of fashion purgatory. Fast forward to the present, and we're witnessing a full-scale renaissance of voluminous legwear. Today's iterations blend nostalgic throwback elements with contemporary fabrics and subtle tailoring tweaks that prevent them from becoming the JNCO-adjacent disasters of yesteryear.

Modern baggy shorts bridge functional performance with street credibility—featuring reinforced stitching, durable materials, and thoughtful details like hidden pockets or discreet branding. Whether paired with fitted tops for balanced proportions or embraced as part of an entirely oversized silhouette, these roomy bottoms deliver the perfect combination of comfort, style, and practical versatility for those who value freedom of movement without sacrificing aesthetic appeal.