Most of the time, the notion of "style icons" conjurs up images from the era of Don Draper, Steve McQueen, and Sidney Poitier. But we'd foolish to overlook the men who have set trends and furthered the style bar in more recent times. Blessed with the gift of hindsight, we can look back and cringe at the trends that we may have lived out in our youth. However, even if the trends were butt at times, the actors, musicians, and athletes who championed them always had next-level swagger that crowned them kings of their time. 

You may have had posters of these dudes hanging in your childhood rooms, or you may have even dressed like a few of these guys. From the golden era of hip-hop to the post-millenium #menswear movement, we looked back to see who lorded over everyone else at their personal apex of steez. These are The 20 Most Stylish Celebrities Every Year for the Last 20 Years.

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