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There's a men's perfume ad you might have seen recently. In it Johnny Depp stands in the desert, squinting off into the distance, a slight scowl playing across his lips like someone's just arrived to lunch half an hour late and didn't even text. He pushes up the sleeve of his black buttonup shirt, revealing a tattooed arm but also a collection of thick silver rings across his fingers, beaded skull bracelets and rosary beads on his wrists. A small silver hoop glints in his earlobe. He looks calm, masculine and – despite wearing all black in the desert heat – cool as an iceberg. This is a man who knows how to wear jewellery. If I were swapped into the photo adorned with sterling rings and topaz baubles, I doubt I'd look half as good. And I'd certainly feel a bit silly. Granted, I am not Johnny Depp. I have not starred in any CGI pirate movies and did not recently purchase a Greek Island for my girlfriend, but none of that should matter. At this point in men's fashion just about anything goes, so why does jewellery remain such a difficult style move for so many of us?

As a writer – not to mention one who writes about men's style for a living – I've never had to worry about appropriate office attire beyond, say, making sure my selvedge denim is appropriately whiskered. I recognize that this is somewhat unusual. For some men, I've heard, wearing non-black socks is enough to raise eyebrows around the office, never mind silver rings and braided leather bracelets. At Holt Renfrew's men's shop, men's-wear director Andrew Lepp is quick to acknowledge that, jewellerywise, the blue-suited Bay Street guy has fewer options than the rest of us. "The business environment is all about the cufflink, the great watch and the tie bar," he says, adding that men in creative fields have more leeway, and even the most buttoned– down professional can branch out on weekends. "I think jewellery just naturally suits itself to a casual way of dressing," he says. Among Lepp's goto brands is David Yurman, which combines classic masculine motifs – feathers, chevrons, cables – with precious metals for a result that's edgy yet luxurious. Beyond that Lepp's philosophy of accessorizing is simple: Less is more. "You don't need a lot," he says with a chuckle. "Not everybody's Karl Lagerfeld, you know?"

Zane Aburaneh isn't Karl Lagerfeld, but he's definitely someone with a keen eye for accessories. Aburaneh runs a couple of eponymous accessory stores and sees the addition of jewellery to a man's wardrobe as a sort of secret style weapon. "What makes you stand out from all the other guys?" Aburaneh asks philosophically. "Is it your eyewear? Is it your bracelet? Is it your watch? Those small accessories are going to make your outfit." Aburaneh wears a black cardigan over a white T-shirt, ripped jeans and battered white sneakers. On his hands are an assortment of chunky silver rings in soft organic shapes. His wrists are layered with bangles in polished silver and braided leather, punctuated by a midcentury Swiss railway watch. "I think a bracelet is the easiest thing because it can hide under a shirt cuff or beside a watch," he says. Among his favourite such pieces are the chunky brass railroad spike cuffs from Giles & Brother and bracelets braided from sturdy rope and clasped with sailing hardware from Dutch brand Pig & Hen. The bracelet is the gateway drug to a fullblown jewellery habit, Aburaneh adds. "Once a guy gets a bracelet then he's looking for other accessories."

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If you squint at that perfume ad you might mistake Johnny Depp for my barber, Jon Roth, but don't tell him I said that. Roth does have a lot of tattoos and a penchant for chunky silver biker rings, but for the record his look is a carefully observed amalgam of punk rocker Mike Ness and pro skateboarder Jason Jessee. He's a stickler for details. "Do you think it's hard for normal guys to look good in jewellery?" I ask him, having stopped by his shop, The Crow's Nest, for a trim. "No," he responds flatly, letting the buzz of clippers fill a dramatic pause before continuing. "It's just like anything, with hair, with clothes, with whatever – it doesn't take a certain type of dude to wear a certain thing from the outside. It's from the inside. I think people are just self-conscious." Could it be as simple as that? It made perfect sense. Selecting the right jewellery is important, but that's easy enough to do with a little guidance. The real key is not caring what anyone else thinks. Just ask the guy with the fistful of skull rings who bought a Greek island for his girlfriend.

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