This oral history study explores the past and present Japanese menswear customtailoring culture. Two master tailors with more than 50 years of experience and two young tailors with less than a year of experience were interviewed about the tailor training process and environment, working conditions, thinking and behavior, and societal and governmental efforts for vitalizing custom-tailoring. The results indicate, first, a 10-year apprenticeship was required in the past, whereas young tailors today must register for three-year professional tailoring classes. Tailors then and now have been trained in a similar sequence of pants, vests, and jackets. Second, regarding working conditions, tailors had to provide gratitude services to their masters for a few years, even after their training ended. In contrast, young tailors today must continue a probationary period after their three-year schooling; however, they experience difficulty with finding tailoring shops for their probation. Third, in terms of thinking and behavior, master tailors learned their trade to earn a living, whereas young tailors today entered the field due to their interests in it. In addition, young tailors want a systematic learning process, whereas master tailors learned their skills while on the job. Last, tailoring academies today are run by tailoring shops and societies. Career exploration programs are offered to elementary and middle school students by the Kobe government in association with the local tailoring society to provide tailoring experiences.