Big Machine Records released "Fearless" to country radio in the United States as the album's fifth and final single on January 4, 2010.

Music critics generally praised the production as catchy and engaging and the lyrics for portraying earnest adolescent sentiments; some retrospective reviews have regarded "Fearless" as one of Swift's best songs.

[1][2] Continuing the romantic themes of Taylor Swift, Fearless is about love and heartbreak from the perspective of a teenage girl, using autobiographical narratives embedded with high-school and fairy-tale imagery.

[6] Swift and Chapman produced the track, which was recorded by Chad Carlson and mixed by Justin Niebank at Blackbird Studio in Nashville.

[9][10] Its arrangement consists of booming drums and chiming guitars[8] alongside mandolin and fiddle;[9] the bridge incorporates a key change.

[8] The musicologist James E. Perone writes that there are "unexpected musical influences" evoking diverse styles of country, pop, folk, and alternative rock in the drums, guitars, and other instruments' "tone colors".

[8] The narrator pays attention to the details, such as how the pavement glistens in the moonlight after a rain, how her date "runs [his] hand through [his] hair", and how she gets excited and nervous anticipating a first kiss.

"[15] Rob Sheffield, writing for Blender, opined that the lyric mentioning Swift's narrator getting caught in a storm "in my best dress" showed that she "likes to make a scene".

Those who picked it as an album highlight included the Hartford Courant's Thomas Kintner, who wrote that its "juicy jangling" production "keeps [Swift] ahead of the game",[35] and The Baltimore Sun's Rashod D. Ollison, who described the sound as "breezy".

[36] Jody Rosen of Rolling Stone highlighted the loud guitars and dynamic refrains,[37] and Jim Abbott of the Orlando Sentinel found the track suitable for "arena sing-alongs".

[38] Others, such as Alice Fisher of The Guardian[39] and Jim Harrington of The San Jose Mercury News,[40] complimented the lyrics for portraying universal feelings evoked by love that appealed to a broad audience.

[41] Ash thought that "Fearless" set the overall tone for the album and found it to incorporate a sense of maturity to the obvious teenage sentiments.

[17] In a less enthusiastic review, Jonathan Keefe of Slant Magazine wrote that the song demonstrated a lack of refinement in Swift's songwriting in how the meter "emphasizes the incorrect syllables of words".

[14] Nate Jones of Vulture (2024) ranked the song 29th out of 245, hailing the way Swift channeled the thrilling emotions despite the lyrics using familiar themes.

[46] Lipshutz selected the opening lines ("There's something 'bout the way/ The street looks when it's just rained/ There's a glow off the pavement") as an example of Swift's abilities to depict romantic whimsy that not many artists could.

[43] Willman contended that the title track's "simpler ambitions" and "typically great melodic line" made it as enduring as other fairy tale–inspired Fearless songs.

For the performance of the song, she donned a silver sparkly cocktail dress and black cowboy boots, played a rhinestoned acoustic guitar, and twirled onstage.

[64] She performed the track donning a golden fringe dress and playing a rhinestoned guitar, which evoked her fashion in the Fearless tour of 2008.

[73] A day prior to the album's release, a snippet of "Fearless (Taylor's Version)", the re-recording of the title track, premiered on Good Morning America.

[73] There are subtle alterations in the details; The New York Times' Jon Pareles wrote that the re-recording omits the organ note 10 seconds into the song,[73] and the commercial music professor Michael A. Lee identified the electric guitar as louder, particularly during the fade-out at the 3:53 mark.