When we look back on photos from the first two decades of the 21st century, it will perhaps be tougher than ever to pick the era from the clothes. These were decades of constant change; when trends cycled in and out more quickly, and men discovered a new appreciation for what they wore and why they wore it.

Those shifts were thanks to these 10 men, who inspired guys the world over to try new things with their wardrobes. It wasn’t all good, and it certainly won’t all look good in the pictures. But god damn it was exciting.

André 3000

André Lauren Benjamin entered the 21st century in clothes as flamboyant as his rhyming style. And for the next 20 years, he continued to push boundaries lyrically as well as sartorially. Long flying against rap’s prevailing style winds, he fashioned a hip-hop spin on golf attire a decade before Tyler, The Creator. With his pocket squares, tie pins and wide-brimmed hat, he also set the template for the #menswear movement (although he wore it with a knowing irony that the Pitti Peacocks never managed to emulate).

Tom Ford

Tom Ford left the 2010s the same way that he started the 2000s; in a black suit with a white shirt, unbuttoned almost to the navel. In the intervening period, he proved not just the power of having a uniform, but also the importance of flexing it – he tried his signature look in double denim, in suede and in all kinds of velvet. Uniforms were big in the first two decades of the 21st century, but unlike Steve Jobs, Mark Zuckerburg and Barack Obama, Ford showed that it’s about embracing consistency, not a sartorial straitjacket.

Jay-Z

The archetypal bad boy done good, Jay Z’s transition from New York coke dealer to world’s wealthiest rapper came with a commensurate shift in his wardrobe (not that we’re saying the two are linked). At the start of the century, his Rocawear label helped define mid-00’s rap’s loose, sportswear-inspired aesthetic – the one we all adopted a decade later. As we did, he shifted to boss-worthy suits from a bevy of in-the-know designers: Dries van Noten, Alexander McQueen, Alessandro Michele’s Gucci. Yet again, it’s time to steal his moves. You might have 99 problems, but your wardrobe needn’t be one.