Big Ush. Big Tyme. Mr. Entertainment. Or ‘Ursher’, if you’re Ludacris. Whichever name you know him by, you’ll know multi-award-winning musician Usher Raymond IV as one of R&B’s smoothest crooners.

But it wasn’t just velvety vocals and dance routines to rival The King of Pop’s that catapulted Usher to stardom – his style moves are also second to none. Here, we chart how his personal style has matured from blinged-out 1990s hip-hop to something more befitting of a modern gentleman, and show you the techniques to steal if you want to look just as slick.

‘Nice & Slow’: Usher’s Style Evolution

No one looks back at what they wore in the late 1990s and early 2000s and thinks, ‘Yup, that was on-point’. Including Usher.

As if pimping his career with the release of his second album My Way wasn’t enough, Usher gave his late nineties outfits the same treatment, piling on brash fur coats, skullcap beanies and enough bling to put Liz Taylor to shame for everything from music videos to red carpet events.

There was the 1998 Billboard Music Awards’ canary yellow ensemble that had us convinced Usher was gleaning style inspiration from Sesame Street, while the chart-topping performer’s head-to-toe leather take on tailoring at 2001’s MTV Music Video Awards was proof that there definitely is too much of a good thing.

Time, however, has been good to Usher. With the release of his top-selling album Confessions in 2004, Ursh gradually shed the Ali G aesthetic in favor of a more polished look to match his pop royalty status. But it’s been in the last few years – since joining the star-studded judging panel on hit US TV series The Voice – that he has really upped the ante. Now, you’re far more likely to see him styling out natty tailoring or slick minimal streetwear than giving Flavor Flav a run for his money.