The game initially allows the player to choose a racer and places them in the Velodrome. From there, they can enter different rooms to decide their next challenge. The player can either challenge the Velodrome trainer to unlock new tricks, or race to unlock new areas and hoverboards. For the challenges, the player must pass through a series of gates before time expires. For racing, the player progresses through tracks on 3 different continents, the US, UK, and Japan. Once all five races on each continent are complete, the player unlocks a "boss race" which unlocks a new hoverboard. There are a total of 18 tracks in the game, with 4 of them being backward versions of existing tracks. During races, the player can perform skateboard and snowboard-like tricks, like grinding on a rail, or spinning in midair, in order to get additional points. If playing a "bully" character, they can also collide with other racers to slow them down, or if not, must avoid being hit by AI racers. A VMU game called TrickStyle Jr. was included with the title, and plays in a similar manner to Snake.
TrickStyle received mixed reviews from critics, with an aggregate GameRankings score of 71.30% for the Dreamcast version and 63.69% for the PC version. Jeffrey Adam Young reviewed the Dreamcast version of the game for Next Generation, rating it two stars out of five, and stated that "TrickStyle is an impressive game to watch, and an infuriating game to play. Track design is sadistic, and AI players are inhumanly adept. Good mostly for increasing your stress level." Brandon Justice of IGN scored the Dreamcast version an 8.8/10, saying that the game "sports the bestart direction I've ever seen in a console racer", and compared the game to Wipeout, although saying it lacked the sense of speed to surpass that series. While calling the game's lack of extras a "letdown", he states that he had a "great time" with the game and that it would "go a long way towards opening your eyes to the possibilities of racing on the Dreamcast." Tal Blevins of the same site rated the PC version 8.5/10, praising its "stunning visuals and incredibly fluid gameplay", but called the soundtrack repetitive and stated that he quickly turned off the music. He also stated that the game was "screaming for" an option to play online against other players rather than just local multiplayer. Ben Stahl of GameSpot gave the game a lower rating of 6.4/10, saying that it was "too easy to beat", and calling the sound effects annoying while praising the music. He praised the "accurate" hoverboard physics, but called the character animations "inhuman". Calling it "perfect-for-a-rental", he nevertheless stated that the graphics were the only thing "great" about the title. Geoff Richards of Eurogamer similarly rated the PC version of the game 6/10, criticizing it as a "direct port" with a "too-easy" difficulty, but calling its visuals "stunning". J.C. Herz of The New York Times called TrickStyle the only racing game on Dreamcast that "inspires hardware lust", calling its hoverboard physics "dreamy" and its visuals "razor sharp and achingly hip". In a 2009 retrospective, Eurogamer called the game a cult classic, saying that the game was "overlooked" in favor of Tony Hawk'sPro Skater.
