Caroline County Public Schools presented proposed revisions to the K–12 student dress code for the 2022–23 school year during the May 9 board meeting. Assistant Superintendent Doctor Monroe said students and principals worked with a student committee to recommend updates intended to reflect current trends while preserving safety and a non‑disruptive learning environment.

Key changes presented included: tops must cover the midriff; bottoms must cover underwear and be no shorter than mid‑thigh; hats, hoods and head coverings will not be permitted inside school buildings except for religious or medical reasons; holes in jeans are permitted regardless of size unless the hole is above mid‑thigh in front or back; and flip‑flops and slides will be permitted at all grade levels, though the presentation urged parents to outfit younger children with safer footwear for recess and physical education.

During board Q&A, Missus Nancy Carson and others expressed concern about permitting flip‑flops for preschool and early‑elementary students, citing trips and falls when younger children are stepped on in line. Doctor Monroe responded that elementary principals had discussed the issue and staff would work with family engagement coordinators to support families and provide clearer language; Doctor Calverick asked staff to revisit wording around the replacement of the term "undergarments" with "underwear" to ensure the policy covers top and bottom garments as intended.

No final vote was taken on the dress code that evening; staff indicated they would return with clarified language and that principals and parents had been consulted during the drafting process.