Sesa was founded in the Marche region of Italy in 1976. During the 1970 and 1980s Sesa, along with other Italian factories, worked for major American corporations to provide handsewn moccasins and penny loafers. With most major companies moving production oversees to Asia in the 1990s, it became rare to find factories that could craft handsewn goods. Sesa's factory thought that this traditional construction technique still needed to be fundamental for their work.

In 2019, Sesa's second-generation owner, Marco Perticari visited Japan to exhibit their collection of artisanal penny loafers and handmade boots. While there he met Masahiro Wakabayashi of TO&CO. Masahiro and Marco quickly collaborated to develop the Sesa Heritage collection, based off classic Japanese inspired footwear from the 1980s. The Sesa Heritage collection is an exploration through archive Sesa models along with classic standards.