Trendsetter: Bob Dylan

Let's face it, we all know polka dots started as a predominately women's clothing fixture. That is, until Bob Dylan came along. The dude just exuded "cool" and no one could deny his style icon status throughout the '60s and '70s, killing it in workwear shirts, suede jackets, and flecked suits. But no one look is more intriguing then Bob Dylan in Rayban sunglasses, frazzled-hungover-hair, and a polka dot shirt. Much like his fellow eccentric musicians who took female-oriented patterns to complete some androgynous look they were going for, he pulled it off perfectly. This started a wave of brands dabbling in polka dots for menswear. Today, brands like Supreme and Engineered Garments have that masculine polka dot look on lock.