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The sport has progressed in leaps and bounds since the creation of Razor scooters in 1999. The first freestyle scooter riders focused mainly on simple tricks, such as no footers, tailwhips, and 360s. More progressive riders such as Jarrett Reid raised the envelope with maneuvers like backflips, frontflips, and 720s.

After the scooter boom of 2000-2001 ended, only a handful of freestyle riders remained. As a result, riders were spread out, and isolated from one other. As a result more variation in the riding was present. In the northwest, there were riders like Silas Henderson, who focused on technical aspects of riding (ex. manual and grind combos). In Southern California, there were park riders who specialized in bigger tricks.

After, riding shifted focus to landing progressively more difficult tricks. If a trick was done sloppily it did not matter; so long as 2 wheels landed on the ground, and the rider did not fall, the trick counted. In park riding, it was rare that a rider would air out of quarter pipes. The emphasis was generally placed on tricks, rather than style.

By 2007, the sport started to move toward more stylized riding as opposed to constantly pushing trick level. Riders pushed themselves to have fluid styles in park. It became common to see videos consisting of many air tricks (especially from Australian riders). This style boss mentality was spawned largely in part by Stan Smirnoff, who pioneered the wide bar movement. Smirnoff forever immortalized himself after describing his bar width as "20 wide, so yeah," in the Transit Scooter Tour DVD.

Currently the sport has regressed slightly into a lesser emphasis on style, however clean landings on tricks are still preferred and favored. Many styles have developed as more and more people discover freestlye scooter riding, and the sport itself is ever changing.