The Shinagawa Shukuba Matsuri festival recently kicked off around the Kyu-Tokaido street in Shinagawa Ward, where a Singaporean woman became the first foreign oiran festival star.
The festival is held annually to re-create the din and bustle of the Shinagawa-juku rest stop during the Edo period.
The "Oiran Dochu" is one of the festival's main attractions and features kimono-clad women parading down the street.
Rachel Leng, a 27-year-old Singaporean selected to be the first ever foreign oiran, caught the attention of many visitors during the festival.
Leng, wearing an extravagant kimono and "takageta" elevated wooden clogs, occasionally walked in the distinctive "soto hachimonji" style, in which the walker's feet trace a sideways arc on the ground.
This year, 45 women, including Leng, applied for the role of oiran. The festival executive committee selected Leng as one of five oiran in a bid to attract interest from foreigners ahead of the 2020 Tokyo Olympics.
Leng has been working at a private equity fund since she moved to Tokyo this January. She studied East Asian studies at Harvard and Duke universities.
"I thought I could learn more about Japanese history and culture by participating in the festival as a cast member, not just as a visitor," she said as her reason for applying for the role.
Leng won Miss Beauty with a purpose of the Miss World Singapore contest in 2013.
Although the festival is similar to a beauty pageant, she spent many hours practicing the oiran walk in takageta ahead of the event.
Even now oiran are perceived as celebrities or fashion leaders or other high status figures.
"It is really eye-opening for me that Japanese do things like this with so much sophistication," she said of learning the history and culture of oiran.
However, even though foreigners consider Japanese customs and culture to be very special, they often have difficulty getting involved in local festivals.
Leng stressed, "It's a great honour for me to take on a key role in a local festival. I think it's a big step forward as Tokyo becomes more international."
An Edo era costume parade, in which about 100 people dressed as samurai, merchants and hikyaku express messengers, will be held on the same street.