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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 favored 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.

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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.

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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.