The inception of baggy jeans is closely tied to the 1980s hip-hop and skateboarding scenes. In these communities, loose-fitting denim offered both practicality—providing freedom of movement—and a distinctive aesthetic that challenged prevailing fashion norms. During the 1990s, baggy jeans became emblematic of hip-hop culture, with artists like Wu-Tang Clan, Aaliyah, and TLC popularizing the style. The oversized silhouette served as a form of self-expression and a statement against mainstream fashion conventions. In the early 2000s, fashion trends shifted towards slimmer silhouettes, leading to a decline in the popularity of baggy jeans. Skinny jeans and more tailored fits dominated the denim landscape, and baggy styles were often relegated to niche subcultures or considered outdated.​

The 2020s have witnessed a significant revival of baggy jeans, driven by a combination of nostalgia, comfort, and celebrity influence. The resurgence aligns with a broader trend towards Y2K-inspired fashion and a preference for relaxed, oversized silhouettes.​ Retailers have reported a surge in demand for baggy jeans. For instance, Pacsun noted that baggy jeans rose from 8% to 80% of their denim sales within a year, reflecting a substantial shift in consumer preferences. The pandemic era emphasized comfort in clothing, leading many to favor looser fits. Additionally, the revival of early 2000s fashion trends has brought baggy jeans back into the spotlight.