During my interview with our cover thing, John O, I asked him how much of a role fashion plays in Diamond Rings. His answer was simple: “Fashion, to me, is just as important as the songs themselves. I don’t privilege any facet, as an artist, above or below. To me it’s all one cohesive whole of who I am or project.”

This is pretty fascinating stuff, mostly because, if you read the feature about one of Toronto’s most rebellious pop stars, you’ll understand that he’s a lot more confident on his new album. His feet fall a little heavier on the ground and it’s very obviously reflected in his style choices. Big, bold shapes, stark lines and chunky details (including what felt like an eight-pound jewel-encrusted baseball cap that I tried to snatch from our shoot without success).

I love it when fashion reflects the person. If a guy is feeling lazy and bummed out by something and sports sweat pants, some old loafers and a cute cap and sunglasses, it feels right. When he’s feeling hot after a couple weeks of eating well and getting lots of sleep and throws on a loud sweater with some well-fitted pants, there’s nothing forced.

It’s when we try too hard and wear things that don’t suit our mood or attitude and try to latch on to a look that’s just not us that things go awry. (If you see me out with my cow-print high-tops, green jeans and leopard-print baseball hat, you’ll know exactly what kind of mood I’m in!)

Our music columnist, Kevin Ritchie, spoke with Michael Jackson’s costume designer, who said MJ always wanted his wardrobe to reflect what was happening on the streets. This example is extreme, but Jackson’s fashion was never contrived; it reflected his latest album’s message and what the kids were doing outside in the real world.

When we shot the Northbound Leather spread, the scrumptious model, Kevin, was slightly uncomfortable with the fetish gear we strapped on him. His posture wasn’t very relaxed and his smiles were a little stiff. But once he mixed in his own button-down black shirt and street shoes, the floodgates opened and all that cuteness came shining through.

I also asked Diamond Rings about one of his greatest musical inspirations, Kylie Minogue. He said, “She’s an inspiration for me more than anyone. She manages to be extravagant but always in a classy way. The clothing that she wears feels unmistakably her.”

And with that, he nails it. Dressing in clothing that’s unmistakably us never goes out of style. — Phil Villeneuve