Loose Fit & Baggy Shorts

97 products

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.