The study performed a comparison analysis of market brand patterns for slim-fit dress shirts and analyzed the body surface development figure of men in their 40s using 3D body scan data and developed slim-fit dress shirt patterns suitable for middle-aged men. The sizes of slim-fit dress shirt patterns showed a slight difference depending on brand. The overlap map of slim-fit dress shirt patterns for brands demonstrates how difference of one-dimensional sizes reflect on two-dimensional patterns. This map provides useful information for pattern design and allows and easy recognition of pattern size differences. A try-on system evaluation through 3D-Simulation allows a grasp of the fitness of neckline and size tolerance of under the arms in front, the silhouette of side lines, and overall fitness in front that also allows analysis of the front/back balance of a shirt in side, the size tolerance proportion in front/back, and the fitness of the arm-hole line. Thus, we obtained try-on results that were equivalent to wearing actual clothing. According to the drafting size suggested in the developed final pattern, the total width was ‘C/2+5.5cm’, and the front was set at 1cm bigger in the size difference of the front and back. The width of the front neck and the back neck was set identically at ‘C/12’, while the width of the front neck was set to ‘C/12+1.5cm’. For the armhole depth, we added ‘C/4+2cm’, and ‘0.5cm and 1.5cm’ for the width of the front and back to anthropometry. The results of the try-on evaluation through 3D-Simulation indicated that the fitness of the final slim-fit dress shirt pattern was superior to available slim-fit dress shirt patterns on the market and evaluated as superior to the types for middle-aged men.