20. Converse "Chuck Taylor" 

Year created: 1932 

Designer:  

The Chuck Taylor shoe is creeping up on 100 years in the game and is the highest selling sneaker of all time. The logo isn't exactly intricate but if it isn't broke, why fix it? The emblem that you see on your Chucks today wasn't completed until 1932 when the official Chuck Taylor signature was added to the mix.