Taylor had already commenced to compose songs for her next album, what would become "Speak Now" (2010), but had also written songs she believed did not correspond with her scope of the record. She included them in a re-release for "Fearless".

Some tracks were written much prior to recording, while others were done subsequently. "Jump Then Fall" was self-penned by Taylor using a banjo and a "feel-good vibe", which, along with its bouncy character, caused for it to be Taylor's favorite song on the re-release. She also reworked the tempo and replaced the guitar-driven instrumentation to piano of "Forever & Always" for the new version of "Fearless". The re-release also included Taylor's only cover on a studio album, a rendition of American rock band Luna Halo's "Untouchable" (2007). She recalled that Borchetta had given her Luna Halo's eponymous second studio album to listen to, and ultimately chose to cover "Untouchable". Taylor altered the song both musically and lyrically, and reworking the arrangement and switching the verses while maintaining the refrains similar, which ultimatively earned her a co-writing credit.

Titled "Fearless [Platinum Edition]", the re-release was announced on September 10, 2009 with a release date of October 27, 2009. It was then pushed forward one day, to a release to October 26, 2009. "Fearless [Platinum Edition]" bore a new collector's cover that altered the background color to black and included a CD and a DVD. The CD had an additional six songs placed prior to the original tracks from the album:

1. Jump Then Fall
2. Untouchable
3. Forever & Always (Piano Version)
4. Come in with the Rain
5. SuperStar
6. The Other Side of the Door

The DVD comprised music videos ("Change", "The Best Day", "Love Story", "White Horse", and "You Belong with Me"), behind-the-scenes videos (for the latter three), over fifty images (photographed by Austin K. Swift, Taylor's younger brother) and backstage footage from the first concert of the "Fearless Tour", and "Thug Story" (a video with rapper T-Pain filmed exclusively for the 2009 CMT Music Awards).