Music and media critics generally praised Swift's stage presence, showmanship, and interactions with her audience, although some thought that she did not possess strong live vocals.

Big Machine Records released Fearless, the second album of the American singer-songwriter Taylor Swift, on November 11, 2008, in North America.

"[5] To conceptualize her tour, she drew on her experiences opening for other country acts including Paisley, Rascal Flatts, Tim McGraw, Faith Hill, George Strait, and Kenny Chesney.

[19] Smeeton conceived the ideas and collaborated with Barry Otto from the production company CT Touring over a few weeks at a studio to execute the designs.

Images that were projected onto the background included "Bavarian castles", "Victorian ivy", flying butterflies, and clouds; each were used in different song performances to accompany their individual meanings and statements.

[22][23] The tour's front of house (FOH) engineer, Russell Fischer, and mixer, Andrea "Vito" Carena, chose Audio-Technica's 5000 Series Wireless System for the lead and background vocals.

Fischer selected other microphones from Audio-Technica for the background vocals (AEW-T5400), systems (AEW-R5200), guitars and overheads (AT4050 Cardioid), and kick drums (ATM25 Hypercardioid).

[31] Before the concert began, the screen showed footage of celebrities including Miley Cyrus, Faith Hill, and Garth Brooks sharing their definitions of the word "fearless".

[41][42] The concert proceeded with a video skit titled "Crimes of Passion" featuring a detective tracing how Swift's name-dropping ex-boyfriends in her songs affected their lives.

[43] Midway through the song, Swift, in a knee-length dress and cowboy boots,[44] went down the aisle toward a rotating B-stage at the floor level, as she hugged her fans and signed autographs for them.

[45] For the performance of "Love Story", the backup dancers wore Victorian clothing and danced to Pachelbel's Canon as a castle backdrop was projected onto the stage.

[46] Swift appeared at the top of the stage, donning a crimson gown with golden accents[33] that critics said to evoke the fashion from the Victorian,[41] Edwardian,[15] or Elizabethan eras.

[47] For the final chorus of "Love Story", Swift hid behind backup dancers as she changed into a white wedding dress and a jeweled headband.

[32][51] The encore for the 2009 shows included two songs: "I'm Only Me When I'm with You" and "Should've Said No";[37] she sang the former with the supporting acts Gloriana and Kellie Pickler as confetti fell down the stage.

[38] Craig S. Semon from the Telegram & Gazette and Kevin C. Johnson of the St. Louis Post-Dispatch deemed her stage presence confident and contagious.

[32][41] The Indianapolis Star's David Lindquist wrote that the show was successful thanks to the moments where Swift shared her life stories and experiences with fans.

"[37] Lynn Saxberg of the Ottawa Citizen thought that the audience was charmed by Swift's sincerity: "She sang with conviction, performed with confidence and you couldn't help smiling at her enthusiasm as she tossed her long, blond curly hair.

The Washington Post's David Malitz wrote that Swift did not have the "most dynamic" stage presence, but he said her performances made the emotional sentiments of her songs more palpable.

[35][48] The Salt Lake Tribune's David Burger and The Florida Times-Union's Tom Szaroleta opined that Swift had an admirable showmanship that eluded veteran performers.

[28][50] Molly Trust of Billboard complimented the set list for balancing between high-energy numbers and mellow ballads and lauded Swift for both her musicianship and her crowd-engaging talents.

[23] Hazel Sheffield of The Daily Telegraph gave the London concert a four-star rating; she wrote that although Swift's vocals "often err on the flat side", she was a winning performer thanks to her relatability and unassuming personality.

[44] Alice Fisher of The Observer thought that despite the emotionally resonant songs, Swift's appeal as a performer with "less obvious" because of her sometimes awkward facial expressions or dance moves.

[31] Nina Braca in Billboard also identified some fashion statements that became iconic: Swift's blonde curly hair locks, "glittery gold outfits", and winged eyeliner.

[66][67] Her headlining performance at Country USA in Oshkosh, Wisconsin, on June 24, 2009, registered 42,000 people in attendance, the largest up to that point during the festival's 14-year history.

[68] Her headlining session at the North Dakota State Fair on July 25, 2009, attracted 50,646 people, marking the first time the festival recorded a daily attendance of over 40,000.

Giving it a 2.5-star rating, Weiss said that the DVD contained some lovely moments, but it was not groundbreaking and offered insufficient insights into Swift's rise to stardom.