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 favour 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.

Usher’s Go-To Looks

Monochrome

When it comes to matters of style, it’s sometimes best to keep things simple. And Usher knows well the power of going monochrome. These days, he’s swapping garish colours like bright yellow and cyan blue for timeless hues such as black, navy and military green.

Whether it’s a lightweight bomber jacket layered over a crew neck tee and teamed with a pair of tailored joggers, or a military overshirt and a straight-fit trouser combination, Usher effortlessly sidesteps (moonwalks?) the potential pitfalls of complex styling by limiting his outfit’s palette.

What’s more, it makes him look taller. He may be one of music’s biggest-selling artists, but he’s by no means one of the biggest. Standing at around 5’8″, Usher gives his frame a serious boost by opting for single-colour getups that help to visually lengthen his silhouette and add vertical inches. Who you calling Shawty?

Get The Look

TIM COPPENS JERSEY AND COTTON-BLEND SHIRT - click to buy AMI ZIP BOMBER JACKET - click to buy FREEMANS SPORTING CLUB CAMP OVERSHIRT - click to buy Short Sleeve Crew Neck T-Shirt - click to buy ACNE STUDIOS JOHNA LOOPBACK COTTON-JERSEY SWEATPANTS - click to buy J.CREW TAPERED COTTON TROUSERS - click to buy

Statement Suiting

Understated isn’t always Usher’s first choice. Especially when it comes to the red carpet. In fact, bold colours and fabrics play a huge part in Mr. OMG’s tailoring repertoire, and we salute him for it.

One of his strongest suits to date is the glittering shiny silver-grey two-piece he wore to the June 2015 Gordon Parks Foundation Awards Dinner And Auction, smartly teamed with a comparatively sober charcoal shirt and loafers. Striking, but in a vastly more sophisticated way than his fur coat, no shirt romps of the past. Equally applause-worthy was his white-on-off-white suited look at 2013’s ASCAP awards – something that could’ve so easily bombed but which Usher managed to pull off with aplomb.

It’s not all star quality though. There’s some sartorial science behind his formal looks too. Swapping out the baggy suit separates that swamped him throughout the early days of his career, Usher’s modern-day tailoring is cut slim to flatter his athletic frame. What’s more, by choosing a shirt in a tonal variation of the same colour as his suit, attention-grabbing finishes and patterns look on-point rather than OTT.

Get The Look

STARLING B SHAWL COLLAR WOOL BLAZER BURGUNDY - click to buy MENENZIES B SLIM-FIT BLAZER GREEN - click to buy MAGNUM VELVET BLAZER GREY - click to buy John Lewis Shawl Lapel Tailored Dress Suit Jacket White - click to buy Kin by John Lewis Stamford Tonic Suit Jacket Emerald Green - click to buy Burton Plain Extra Slim Suit Jacket - click to buy

High Style Headwear

From tight knit beanies to coonskin caps, Usher’s headwear choices have made nearly as many headlines as his music. And while it was short-brimmed fedoras that Ursh favoured during the Confessions era, he’s since branched out into snapbacks, bowlers and, recently, a military style beret, which looks a hell of a lot better than it sounds.

Hats, for men, are a bit like Usher’s falsetto: insanely difficult to get right. So, if you’ve been looking for a blueprint to getting it right, pore over some of this guy’s wins to spur you on.

Key to Usher’s success is matching the tone of his hat to his attire; not in terms of colour but its position on the smart-casual scale – i.e. a burgundy beret with a green military overshirt makes sense. The same goes for a felt bowler or fedora with a perfectly-tailored black suit.

Get The Look

RICK OWENS DRKSHDW LEATHER AND SATIN BASEBALL CAP - click to buy LOCK & CO HATTERS GROSGRAIN-TRIMMED RABBIT-FELT HAT - click to buy LAROSE RABBIT-FELT TRILBY - click to buy ASOS Bowler Hat In Black Felt - click to buy Reclaimed Vintage Straw Boater Hat - click to buy Goorin Mad Dog Pork Pie Hat - click to buy

Key Piece: The Leather Jacket

Usher’s style is anything but conventional. But that’s not to say this man doesn’t know his menswear classics. Effortlessly cool and brimming with musical pedigree, the leather jacket is a true statement piece that music legends have turned to for decades – including Usher’s hero, Michael Jackson. MJ and Ursh have more in common than several octaves-spanning vocal ranges and killer dance routines; they both know the power of the black leather jacket, too.

From biker to bomber styles, Usher takes full advantage of the jacket’s one part smart, one part edgy formula to dress up a casual crew neck tee and jeans combo.

Want to build a leather line-up like his? Look for interesting finishes (think padding, perforations, unique distressing) and statement hardware to make this wardrobe mainstay your showstopper.

Get The Look

SPITFIRE LEATHER BIKER JACKET BLACK - click to buy CAMERON CONTRAST BOMBER JACKET INDIGO - click to buy MONITALY RAGLAN ZIPPER JACKET - click to buy Balmain Motorcycle Jacket - click to buy Neil Barrett Embroidered Star Leather Bomber Jacket - click to buy Versace Collection Quilted Leather Bomber Jacket - click to buy

Final Word

While he might not have the fashion profile Kanye does, Usher can more than hold his own in the style stakes. No matter if it’s an all-black outfit or eye-catching suit, Ush is able to seamlessly transition between classic and statement with ease – and that deserves major props.

Have you got it bad for Usher’s standout style? Or maybe you’d rather just see his wardrobe burn?

Share your two cents below.