Converse Chuck Taylor All Star (1917)

The most sold shoe in history with over 1 billion pairs. Chuck Taylors were basketball shoes from 1917 to the 1970s, then became the uniform of punk rock (Ramones), grunge (Kurt Cobain wore them on Nirvana's last tour), and every counterculture movement since. They're the only shoe equally at home on a basketball court in 1950, a punk show in 1977, and a fashion runway in 2025. The design hasn't meaningfully changed in 107 years. Nike acquired Converse in 2003 for $309 million — a steal for a brand that now generates $2.4 billion annually. The Chuck Taylor is proof that simplicity, when it's right, is permanent.