Not only Japanese sweets but also kimono convey beautiful seasonal messages to us. Practitioners will wear a specific kimono for formal tea gatherings. They also change their kimono depending on the season and the type of occasion. By exploring practitioners’ and kimono dealers’ voices, this chapter examines the meaning behind the kimono in relation to Japanese gender roles and norms. This chapter will first introduce how kimono have evolved throughout the period of time. After exploring the clear gender roles in kimono design, it also examines the current efforts made to attract the younger generation in Japan considering gender free designs and environmental issues.