During the Second World War, the United States government regulated civilian apparel when they froze styles at their spring 1942 levels. It is relatively easy to observe the wartime impact on apparel styles in the slim silhouettes and absence of style details such as cuffs, leg-of-mutton sleeves, and double-breasted jackets. Less transparent may be how the war influenced apparel retailers’ merchandise assortment and pricing strategies. Using archival records from the National Archive, specifically records of the United States Office of Price Administration’s Apparel Enforcement Division housed at the National Archives in College Park, Maryland, this case study explores the complexities of retail management during the Second World War. These records indicate which retailers were suspected, investigated, and convicted of pricing violations during the war. Additionally, they provide a glimpse into retailer’s merchandising and pricing strategies while the nation was at war. Within this historic context, students will come away with a better understanding of the complexities of this situation by calculating markup, price increases, and averaging costs.