of 21

The Most Memorable (and Stylish) Headwear in Music History

A musician’s journey to becoming a cultural icon is usually filled with experimentation and creative expression. Anyone who is into fashion also knows that along the way, an artist’s personal style will play a huge part in the grander scheme of things. One thing in particular we’ve always noticed when it comes to musical tastemakers is the ongoing trend of establishing iconic headwear. It might sound a little strange, but can you even think of Frank Sinatra, Flavor Flav, or Willie Nelson without picturing their trademark dome apparel?

Take a look at some of the most memorable hats and headwear that we’ve seen throughout music history, ranging from Jimi Hendrix and Keith Richards to Run-D.M.C. and LL Cool J. If you’re still looking for a pretty ill Halloween costume, don’t be afraid to use this list as a source of inspiration.

Click to start the list

Latest News