Dressed for School

Walter H. Lillard, Tabor’s fifth headmaster, introduced the school’s first dress code when he arrived in 1916. He traced the idea to his college summers working as a counselor at Camp Pasquaney in the foothills of New Hampshire’s White Mountains.

At the all-boys camp, uniforms flattened social distinctions. Boys from different backgrounds dressed alike and, in Lillard’s view, learned to live by the same values. What stayed with him was a vision of community built not on privilege or pedigree, but on shared expectations and responsibilities.

When he came to Tabor, Lillard set out to apply that principle to a preparatory school setting. In outlining his vision for campus life, he wrote of his intention to “keep the enrollment well salted with scholarship boys and treat all boys alike.” Dress would become the clearest expression of that philosophy. If students were to live as equals, he believed, they would first have to look the same.

“The loose-fitting sailor’s blouse of the Navy is a very sensible and very inexpensive garment for the wear and tear of the daily program,” the 1920–1921 school catalog explained. Before starting at Tabor, students sent their measurements to the school. When they arrived, their clothes were waiting for them at the Marion General Store.

Boys wore blue and white working uniforms during the day before changing into formal blue cadet suits for dinner. Dress expectations were similar at the Girls’ School, the separate division Lillard established as part of his 1916 reorganization. Nautical clothing was fashionable at the time, echoing British naval styles. The pullover shirts, known as “middies,” nodded to the midshipmen who wore them.

“The girls at Tabor wore blue serge [middie] blouses and pleated skirts in winter,” recalled Phyllis Morse Mendell, Class of 1926. “In the warm weather, we changed to white middies and skirts, always with the carefully folded black silk tie with a square knot.”

Despite the enduring image of early Tabor, students were not perpetually dressed in uniform. School catalogs from the mid-1920s encouraged them to pack “ordinary civilian clothes” for dinners and weekends. 

By the decade’s end, boys increasingly wore street suits outside of the classroom, while girls adopted contemporary styles, including the bobbed hair and knee-length dresses of the flapper era. Knit sweaters emblazoned with a large maroon “T” became a common sight for both, blending school identity with personal expression.

When James W. Wickenden succeeded Lillard in 1942, the sailor uniform no longer defined every aspect of daily dress. A clearer division had taken hold: Uniforms remained practical attire for co-curricular life—sailing, shop work, and the military drill program— while jackets and ties became standard in classrooms.

Wickenden’s long tenure emphasized order and visible standards. Daily expectations were closely enforced and grooming was regulated alongside clothing. A school barber ensured hair stayed neatly off the collar. Students influenced attire for special occasions— seniors had a say in what was worn for dances and Commencement—but routine dress left little room for negotiation.

Drill, introduced during World War II as part of national preparedness efforts, replaced Chapel during the war years and remained a fixture afterward. Over time, the sailor uniform became largely ceremonial—reserved for drill, public events, and occasions such as United Nations Day rather than everyday instruction. As the 1947 Catalog clarified, “Although Tabor boys wear uniforms for a part of the day, and partake of organized drill at intervals, the school is in no sense a military or naval school.”

One of the most consequential wardrobe shifts of the Wickenden era came in 1955, when the school introduced its first official blazer. Negotiated by Bob Jones ’55 and the Student Council—with Mrs. Wickenden serving as intermediary—the black jacket, with gold buttons and a newly designed Tabor crest, drew inspiration from British school traditions. It remained a staple into the 1990s, and the crest took on an increasingly prominent role in school branding.

The sailor suit was fully phased out in 1967, when drill—its last stronghold—switched to khaki uniforms following a student campaign to model attire after the U.S. Naval Academy.

“Instead of the outdated blues we wear in the fall,” a Log writer asked, “why can’t we wear khakis with a genuine tie that does not come undone in the wind? If they’re good enough for Annapolis, why can’t they be good enough for us?” 

As the 1960s drew to a close, forces beyond campus began to reshape how students dressed. National conversations about youth culture, authority, and self-expression filtered into school life, loosening the uniformity that had defined earlier decades. What students wore—inside and outside the classroom— began to change more quickly, reflecting a broader skepticism toward rules once taken for granted.

The return of co-education in 1979, under Headmaster Peter Webster, brought new clarity—and new tension—to dress expectations. Jackets and ties remained standard for boys. Girls were expected to wear skirts or dresses, with pants permitted during the winter months.

Fashion did not always comply. Culottes and knickers—the billowing, skirt-like pants enjoying renewed popularity—appeared across campus before being prohibited in 1981. In 1986, girls lost the ability to wear pants in winter after administrators cited repeated violations of formal standards. Although boys and girls often accused the other of having it easier under the rules, the restriction united many in shared opposition.

“A tie is inane,” one male student opined in The Log. “A skirt when the temperature becomes unreasonable is a cruelty.”

The formal framework remained largely unchanged through the mid-2010s, even as styles shifted. Hemlines rose and fell. New trends tested the boundaries of what qualified as appropriate school attire, prompting clarification from administrators and reciprocal frustration from students.

“One of the things that happens with these dress codes, somebody in the fashion world invents something and there’s so much gray area,” says Dean of Student Life Jay Houck, who joined the faculty in 1987. “We try to make the policy as fair as we can for everyone.”

For many years, students were expected to wear formal dress in the dining hall for all weekday meals. That expectation eased near the end of Headmaster Jay Stroud’s tenure, when casual attire was permitted at dinner—a shift welcomed by athletes coming off late practices.

Stroud’s successor, John Quirk, introduced a broader recalibration. Under the motto “dress for success,” the school adopted a more business-casual model that distinguished between “Standard Dress” and “Formal Dress,” which was reserved for chapel days and other special occasions. 

That framework continues today. “Standard Dress prepares students to dress appropriately for more relaxed workplace environments and outings,” Life at Tabor explains. “Formal Dress occasions prepare students for environments with international dress code norms like college or job interviews, corporate events, and global traditions.”

Fashion is fluid by nature, expressive and quick to change. Dress policies, by contrast, are designed to be steady, cohesive, and clear. The story of dress at Tabor lies in how those rhythms have met—students testing expression, the school refining expectations, and both adjusting, again and again, to the moment at hand.