Skating really died down in the last year of the 90’s. Sure, there were people that skated but it hadn’t exploded to the levels of today. If you were skating in 1999 its because you loved the sport not because you thought it was the “in thing” to do. This started to reflect in the fashion. As you can see the Santo’s shoe pictured was very plain and chunky, not the greatest casual wear shoe but good for skating. Jeans were baggy and the shirt design plain. Also, keep in mind this was a good 3 years before the birth of Nike SB and all the retro fashion that would follow. Take a trip back to simpler times with the 1999 ad below.
