There are plenty of "trendsetters" this time of year, whether they're celebrities at awards shows or street style favorites on Tumblr, but we're looking back in time because there is always someone who did it first. So let's differentiate between the trendy, well-dressed dudes now from the real OG trensetters from back in the day. The pieces you love so dearly were adorned first and made cool by guys old enough to be your great grandpappy. There are very few trends that weren't once fashionable long ago, and we certainly aren't mad at that.

Style icons like J.F.K., James Dean, and Jimi Hendrix were true visionaries when it came to setting style trends they knew fit their look, no matter how unorthodox it may have been in their time. They probably didn't think it would carry over generations and generations to become staples in style-savvy guys' everyday look. So, do you know Who Wore Your Favorite Trends First?