17. Vans Sk8-Hi
The first skateboarding shoes were just deck shoes by another name - check the Vans Authentic and Era for details. The Sk-8 High, or Style #38, changed everything. Introduced in 1978, it was inspired by early (post-Chuck) basketball shoes and provided more aggressive skaters with ankle protection as well as more support. Modern skatebarding required a more advanced shoe - and here it was.