Fearless received generally positive reviews, earning a collective score of 73 out of 100 on Metacritic. Stephen Thomas Erlewineof AllMusic believed Swift abandoned teen pretenses, styling herself after Shania Twain and Faith Hill prior to becoming divas. He added that Swift presented herself as a "big sister instead of a big star", pointing "Fifteen" as a prime example of it.
Despite noting the album's pop music elements outweighed its country music elements and calling it "one of the best mainstream pop albums of 2008", Erlewine said Fearless "never [felt] garish, a crass attempt at a crossover success". Ken Tucker of Billboard wrote, "Those who thought Taylor Swift was a big deal after the release of her first record be prepared: She's about to get way bigger.
Though they're written by a teenager, Swift's songs have broad appeal, and therein lies the genius and accessibility in her second effort."James Reed of The Boston Globe believed Swift's charm was in her songwriting and that honesty is what separated her from other teenage starlets at the time who relied on "big-name producers, songwriters, and Disney shows for a music career." Drawing similarities between her ability to "blur the line between commercial country and Top 40 radio", Reed compared the singer to a younger version of the Dixie Chicks. Top music critic Robert Christgau graded the album an A–.
He was not fond of the album's overall message, which he declared to be "You have to believe in love stories and prince charmings and happily ever after", but was immensely impressed with Swift's songwriting, calling her "an uncommonly-to-impossibly strong and gifted teenage girl".
Adding that she imparted realism similar to that of a diary in all of Fearless 's songs, he believed set the bar too high for other teenage artists and role models. Leah Greenblatt of Entertainment Weekly stated, "A button-cute blond teen with a pocket full of hits — sounds like the early aughts all over again, no? But aside from sharing, possibly, a box of Clairol, there is nothing remotely Britney- orChristina-esque about Swift." Greenblatt presumed that at the time her fan base would remain young females due to her way of communicating with them, but would grow over time.
Alexis Petridis of the United Kingdom magazine The Guardian had mixed opinions about the album, for he thought it was certainly "bland and uninventive", yet executed incredibly well. Over the course of listening to it, he queried if more music of the sort was needed, and concluded that "the feeling that the world is going to answer your query in the affirmative swiftly overwhelms you."
Jody Rosen of Rolling Stone called Swift "a songwriting savant with an intuitive gift for verse-chorus-bridge architecture that [...] calls to mind Swedish pop gods Dr. Luke and Max Martin." Rosen attributed Swift's particular charm to in how intertwined almost impersonal professionalism with intimate and real confessions. Jonathan Keefe of Slant Magazine believed Fearless pointed out that Swift was capable of having a long musical career.
However, Keefe was disappointed in the album, for it did not showcase significant refinements as she did on Taylor Swift; but, with an immature voice and young age, to him, Swift still had enough time to perfect her craft and make a great album. Josh Love of The Village Voice wrote, "This remarkably self-aware adolescent's words don't falter, masterfully avoiding the typical diarist's pitfalls of trite banality and pseudo-profound bullshit." Chris Richards of The Washington Post said, "In Swift's world, every song is a radio-ready charmer, confirming the 18-year-old's ability to pen a gaggle of consistently pleasing tunes."
He noted Swift's voice was only minimally twangful and her vocal delivery was sugary enough to receive heavy rotation onRadio Disney, yet poised enough to do the same CMT. He also felt Swift was a talented songwriter, but her consistency sometimes fell into uniformity.
