In 1918, cousins C. N. Williamson and E. E. 'Colonel' Dickie, along with a few friends, established the U.S. Overall Company in Fort Worth, Texas, laying the foundation for their future ventures in workwear manufacturing.

The Williamson-Dickie Manufacturing Company, later known as Dickies, was founded in 1922 by Texans EE “Colonel” Dickie, CN Williamson, and C Don Williamson. It started as a bib-overall manufacturer.

In 1940, Dickies shifted their production to focus on 'Soldiers of Supply' in preparation for America's involvement in World War II. They produced over 9 million uniforms for US soldiers abroad during the war.

In 1955, Dickies advertised its work clothes as 'Wear-approved by millions' and highlighted features like better looks, longer wear, neater fit, and easier action. The company's products gained popularity post-World War II, resonating with consumers transitioning from military uniforms to workwear.

In 1960, Dickies built a manufacturing plant in Belize, which was later destroyed by hurricane Hattie but subsequently rebuilt to meet the growing demand in Europe and England.

In 1967, Dickies introduced the iconic 874 twill work pant made with a durable blend of 65% poly and 35% cotton. These pants were highly durable and became a best seller, remaining popular to this day.

By April 1977, Williamson Dickies acquired almost 30 percent of the General Diaper Corporation, a major diaper manufacturer. This strategic move allowed Dickies to expand its presence in the diaper market and diversify its business.

In 1978, the Blessings firm moved its headquarters from New York City to New Jersey.

In 1987, the publishing division of Blessings Corporation was sold to Parenting Unlimited, an investment group.

In the late '70s and '80s, Dickies gained popularity among Black and Latinx communities in Southern California, transitioning from workwear to streetwear. Influential groups like N.W.A wearing Dickies in music videos helped solidify the brand's image as a streetwear staple.

By 1990, Dickies had been embraced by subcultures on both the West and East Coasts of America. Rap artists and skateboarders started wearing Dickies for their loose-fitting style, durability, and representation of a 'taking-care-of-business' attitude.

Tupac Shakur's group Thug Life popularized Dickies' denim bib overalls as a symbol rooted in community history. The trend of wearing overalls spread globally in the '90s, becoming a fashion statement embraced by various demographics.

In 1994, Blessings Corporation sold off its Geri-Care division for virtually nothing in exchange for tax relief after experiencing declining profits.

Skateboarding culture in the '90s saw the mainstream popularity of Dickies among skaters, symbolizing durability and affordability. Skate videos like Welcome to Hell featured riders sporting Dickies, solidifying the brand's association with the skate scene.

In 1998, Dickies decided to enter the Asian market to compete with cheaper imports and expand its market share. They partnered with Japanese firm Itochu to distribute their products in Japan, a strategic move to establish a presence in the affluent Asian nation.

In 1999, Dickies acquired Workrite Uniform Co., a California-based company specializing in flame-retardant workwear. This acquisition allowed Dickies to expand its product range and cater to industries such as oil, gas, and hazardous chemicals.

The fashion evolution from the 2000 film to the 2020 series of High Fidelity showcased the enduring appeal of Dickies logo shirts. The brand's popularity fluctuates with trends, as seen in the Y2K nostalgia and the influence of iconic characters like Rob Gordon.

Eminem's fashion choices, including Dickies denim bib overalls, pay homage to hip-hop style and cultural references. By incorporating workwear elements into his outfits, Eminem adds a unique twist to his stage presence and persona.

Junya Watanabe's collaboration with Dickies in 2006 brought blue-collar aesthetics to high-end fashion runways, challenging traditional suit styles. The partnership highlighted the influence of workwear on designer collections and the fusion of different fashion genres.

In 2008, Williamson-Dickies acquired the Canadian Kodiak Group Holdings Inc.

In 2013, Dickies acquired Walls.

In 2014, Jerry Leigh of California became the exclusive licensee for Dickies Girl juniors' apparel.

In 2017, VF Corp acquired Dickies, a renowned workwear brand, known for its quality and affordability. VF Corp is the parent company of various global brands like Vans, The North Face, and Timberland.

In October 23, 2020, an Italian Riviera Tour supported by Dickies took place. The tour was organized for skaters by the Dickies brand, showcasing their support for skateboarding culture.

Dickies workwear became popular among rappers and athletes, who added their own style by wearing cropped pants and showcasing the durability of the brand. The influence of hip-hop and skate culture on fashion is significant, making Dickies a staple in both subcultures.

In 2022, Dickies will mark a century of crafting innovative workwear that is recognized for its performance, durability, and comfort. This milestone signifies the brand's long-standing legacy and commitment to quality.