Costume evolution of Jessie in the parks and live appearances (1999-present).
| Picture | Years | As seen in | Notes |
|---|---|---|---|
 |
1999 - 2023 | Disney parks | Jessie's first look. It phased out in 2020 in Hong Kong Disneyland when it closed due to the COVID-19 pandemic, cruises in summer 2021, the US parks in early 2022, Tokyo in summer 2022, Paris in May 2023 and Shanghai Winter 2023. |
 |
2001 - 2011 | Disney on Ice: Toy Story 2, 100 Years of Magic, The Magical World of Disney On Ice and All Star Parade. | This alternate atmosphere costume was only used in Disney on Ice shows for a decade. Like Woody, she also has the capability to remove her hat. |
 |
2009 - present | Disney On Ice and Disney Live! shows | A face character version of Jessie. This version debuted in Disney On Ice: Let's Celebrate in 2009. |
 |
February 22, 2021 - present | Disney California Adventure | Following Woody's redesign, Jessie, along with Buzz, becomes more accurate to the animated version. This version debuted at Hong Kong Disneyland in February 2021 before appearing in Disney Cruise Line in July of the same year.
This version was then introduced to Disneyland Resort Paris in January 2022 in time for its 30th anniversary during the commercial before being used there regularly beginning in March 2022. As well, it was shown in a promotional picture for the Disney Adventure Friends Cavalcade at Walt Disney World on January 27 of the same year. It was then introduced at Disneyland in February 2022, later at Tokyo Disneyland in July 2022, and then at Shanghai Disneyland in December 2023. |
