In the 90's the most popular shoes were big basketball shoes that were heavy and had a lot going on.
From 1985-2014 Jordans were very popular and almost every colorway sold out and most would resell for $300-$700 and some would sell for up to $2000
After that at about 2010 the popular shoes changed and now everyone wanted a very light shoe that was minimal and knit uppers became popular.
In 2013 Adidas boost came out and everyone wanted to wear Adidas shoes because they had boost. The Adidas Ultra Boost became the most popular shoe because it was so comfortable.
Vans have also been very popular for a very long time and since they are very simple you can wear them with everything.
In the present day (2018) the new trend of shoes is "dad shoes" or shoes that look big on your feet and that are ugly but since Kanye West made the Yeezy 700 and 500 and Balenciaga made the Triple S they are popular now.