Booker Taliaferro Caldwell, successful tailor, men’s wear entrepreneur, and son of John and Nannie E. Caldwell, was born on January 23, 1923, in Neches, Texas (Anderson County). Caldwell’s father, also a successful businessman, owned a sawmill company, cotton gin, and tomato shed between Anderson County and Cherokee County. At one juncture in the early part of the twentieth century, John Caldwell was one of the largest land owners—Black or White—in East Texas. He married twice and had sixteen children between his wives Nannie Caldwell and Josephine Caldwell.
Booker Caldwell spent his childhood working in his father’s businesses. He also earned commissions selling suits through a mail-order tailoring company as a teen and became interested in the trade. He attended grade school in Cuney, Texas, and later graduated from Clemons High School. Caldwell followed in his sibling’s footsteps by attending Mary Allen Junior College in Crockett. In 1941 he enrolled in Prairie View State Normal and Industrial College (now Prairie View A&M University). He participated in track and was a substitute runner on the relay team that placed first at the Drake Relays in 1943. A few days after the win, Caldwell and some members of his team were drafted into the United States Army during World War II. He fought in the Battle of the Bulge and, after completing military service, returned to Prairie View to finish his studies in tailoring and agriculture.
During the last days of the semester he met his future wife, Jean Hines, a native of Houston, Texas. After graduating in 1946, Caldwell managed an alteration shop and taught tailoring in the Texas cities of Elkhart, Dayton, and Liberty (at a county vocational school). By 1952 Caldwell had opened a tailor shop, and during that year he married Jean in Liberty. The couple moved to Houston in the mid-1950s and later had two children, Kirbyjon and Dorothea.
Caldwell opened a tailor shop in the Fifth Ward on 2765 Lyons Avenue, which proved to be a lucrative spot. Lyons Avenue was a main thoroughfare from the 1930s to the 1960s and home to more than forty Black-owned businesses. Within a few years, Caldwell relocated to the 3300 block of Lyons, luckily, near Club Matinee and the Crystal Hotel, venues where Black entertainers from across the U. S. flocked to entertain their fans and lodge during segregation. Whenever possible, Caldwell would visit the two establishments and leave his business card with famous personalities. The Deluxe Theater, a segregated movie house, was across the street.
Caldwell often benefited from referrals from Black businessman, Don Robey, owner of Duke-Peacock Records, located in the 4400 block of Lyons Avenue. As a result, he became the “clothier of choice because his shop was located in the right place and he built a reputation for great styling.” During his heyday in business, Caldwell served such clients as James Brown, B.B. King, Bobby “Blue” Bland, Ike Turner, Johnnie Taylor, Buddy Ace, Junior Parker, Clarence “Gatemouth” Brown, Lightnin’ Hopkins, and many others. Though he profited from clothing celebrities, ninety percent of his business came from local sales. Before the advent of discount retail stores, Blacks came from all over the city to get their dress clothes from Caldwell’s Fine Tailoring. Caldwell later expanded his suits and other fine clothing line with the addition of shoes and accessories.
Caldwell’s store was burglarized at night on several occasions in the 1960s, but he never retaliated or retreated despite these attacks. In the 1970s his business began to decline as a result of overwhelming poverty in sections of the Fifth Ward, middle-class Blacks moving to the suburbs, and the arrival of discount retail stores. Caldwell relocated his business to the Third Ward inside the Eldorado Building on Elgin Street. This site was home to the famous Eldorado Ballroom hailed as one of “the finest showcases in the South” for live Black music.
In 1999 Caldwell was honored with the Heritage Award from the Houston Citizens Chamber of Commerce for his lifetime achievement in business. He closed the store in 2004 after fifty-plus years of outfitting many Black musicians and celebrities throughout his career while also providing top-of-the-line clothes for many Black Houstonians.
Booker T. Caldwell died of kidney failure and congestive heart failure on July 14, 2011. He and his wife were members of Windsor Village United Methodist Church in Houston, where his son Kirbyjon was pastor. His clients, family, and friends described Caldwell as a devoted husband, father, grandfather, businessman, friend, and Methodist. He was buried in Houston National Cemetery.