When most people think about the collision of workwear and streetwear, Carhartt is the first name that gets dropped. But lurking in the same lane, just as influential—if not more so in certain corners of culture—is Dickies. The brand’s tough-as-nails reputation was built on construction sites and factory floors, yet it has found a second life on sidewalks, stages, and skateparks.
This isn’t just a story about pants that don’t rip and shirts that don’t fade. It’s about how a century-old Texas workwear company managed to embed itself in hip hop, skateboarding, and global fashion.
Blue Collar Beginnings
Founded in 1922 as Williamson-Dickie Manufacturing Company, Dickies was born to outfit American workers with durable, functional garments. Its 874 Work Pant—introduced in the ’60s—epitomized the brand’s ethos: affordable, rugged, and built to take a beating. For decades, Dickies was synonymous with uniformity, supplying everyone from mechanics to military personnel.
It was this ubiquity and practicality that ironically set the stage for Dickies’ cultural crossover. What started as gear for laborers became blank canvases for new identities.
From Job Sites to Street Blocks
In the late ’80s and early ’90s, West Coast hip hop latched onto Dickies. Artists from Los Angeles neighborhoods embraced the brand’s work pants and button-ups as part of their uniform, pairing them with oversized flannels, crisp white tees, and Nike Cortez sneakers. The look became synonymous with authenticity, toughness, and street pride.
At the same time, skaters across the U.S. and beyond discovered Dickies for the exact same reason tradesmen loved them: durability. A pair of 874s could withstand countless slams, grinds, and scrapes—something skate-specific brands couldn’t always promise. The stiff fabric and loose fit also gave skaters the mobility and protection they needed.
Dickies didn’t engineer this transition—it happened organically. Workers wore them to work, rappers wore them to rep, and skaters wore them to shred. By the mid-’90s, Dickies had cemented itself as a cultural staple.
Skateboarding and the Dickies Program
Recognizing its grassroots adoption, Dickies leaned into skateboarding with intention in the 2000s. The brand launched its skateboarding program, supporting skaters who embodied the same toughness and DIY ethos Dickies had always represented. The Dickies Skate Team grew to include heavy hitters like Vincent Alvarez, Jamie Foy, and Ronnie Sandoval—athletes known for raw styles and heavy street footage.
Dickies’ investment wasn’t just about slapping logos on pros. The brand collaborated with skaters to refine product fits and functionality, releasing Dickies Skateboarding apparel that blended the classic 874 aesthetic with skate-specific tweaks: reinforced stitching, flexible fabrics, and slimmer silhouettes that appealed to modern riders.
Through events, film projects, and team edits, Dickies carved out its own space in skateboarding—proving it wasn’t just a legacy brand resting on workwear heritage, but an active participant in youth culture.
Fashion Recognition (Or Lack Thereof)
Despite its deep roots in hip hop and skateboarding, Dickies has never quite enjoyed the same fashion-world shine as Carhartt. Carhartt WIP (Work In Progress), its European streetwear arm, rebranded the workwear image into a high-fashion favorite. Dickies, on the other hand, took a more understated route, letting culture dictate its relevance rather than aggressively marketing itself as streetwear.
That hasn’t stopped designers and brands from pulling Dickies into fashion’s spotlight. From Supreme collaborations to runway adaptations in Paris and Tokyo, Dickies has been reinterpreted countless times. Yet the brand still carries a rawer, grittier association—more tied to authenticity than trend-chasing.
Why Dickies Matters
The beauty of Dickies lies in its duality. It’s as much at home on a job site as it is in a skate video. It can be worn creased and polished at a backyard cookout, or shredded to threads on a handrail in downtown L.A. It’s not trying to be luxury—it’s real, it’s rugged, and it’s been adopted by those who value function as much as style.
Whether or not fashion circles give it the same respect as Carhartt, Dickies has achieved something even harder: permanence. Few brands can claim to be beloved by construction workers, rappers, skaters, and style heads alike.
That’s not just workwear. That’s culture.