Taylor Swift received positive reviews from contemporary critics. Jeff Tamarkin of AllMusic Swift as a "a fresh, still girlish voice, full of hope and naïveté, but it's also a confident and mature one".
He said her "talent to be reckoned" was portrayed through the songs "Tim McGraw", "The Outside", and "Mary's Song (Oh My My My)". Tamarkin criticized producer Nathan Chapman for applying "a gloss that not all [songs] really require and in some cases would do better to shed".
Rick Bell of Country Standard Time gave a positive review, saying that Swift had "smart songwriting" and that "her deeply personal, self-penned songs, particularly 'The Outside' and 'Our Song'" were "stirring." He compared her sound to Cyndi Thomson and Hilary Duff.
Chris Neal of Country Weekly said that Swift "demonstrat[es] an honesty, intelligence and idealism with which listeners of any age will be able to connect" and added that "the more thoughtful material suggests a talent poised to last well past high school." Ken Rosenbaum of The Toledo Blade wrote Swift "deftly handles lyrics and subjects in that shadowy area between teenager and womanhood.''
