Style Challenge: Denim Jackets

Style Challenge: Denim Jackets

Don’t blink, or else you might miss the perfect transitional weather that we’ve been blessed with lately.

But there’s no way that you’ve missed the accompanying hordes of denim jackets that now flock to Toronto’s streets. Think of it as the 6’s unofficial spring uniform (because with our penchant for losing at sports, no team’s jersey is ever going to work out).  

The jean jacket, once popularized by a history of rebellion, has seen a resurgence in popularity across generations for good reason. Besides tapping into a trend for “nowstalgia” (coined by the Guardian as millennial referencing of times just gone), denim jackets read as authentic. Rocking denim outerwear can guarantee you exude a certain level of cool. Unless you’re JT at the 2001 AMAs, that’s just a denim disaster.

So, with the jean jacket having been a style staple every decade since James Dean’s Rebel Without a Cause, how do you find the right denim to don on the streets? The key is to feel comfortable in it — that’s the jean jacket ethos. Even the styling of it is in the dye of the denim-holder (hold your applause). And that could include removable pins and patches of your fav teams too, at least those aren’t as permanent a reminder of the losses to come.

Keeping that in mind, in this month’s jean jacket challenge, we share with you how we’ve styled our denim and the design behind our choices:

Steven Lee

Photographer & Graphic Designer

Denim Jacket: Craig Green


This is the first piece that I ever bought from Craig Green and I like to think that it’s the one that started my love affair with the brand (if you’ve read my previous posts, you’ll understand how highly I admire him). I mean, how could it not? This denim jacket is unlike anything I’ve ever seen before. When wearing a statement piece like this, I like to pair it with classic basics. A white t-shirt, a pair of black khakis, and black loafers do the trick. Remember, you don’t want your outfit to be too busy or look overdone.

Sean Pollock

Art Director

Denim Jacket: Levis


I’ve always wanted a classic Levis denim jacket, similar to the one my dad wore when I was a kid. There’s just something about them that embodies an inherent old school cool. The inspiration for this look was Ivy League meets 80s edge. For this reason, I paired my jacket with a cotton oxford shirt, ankle length trousers from Uniqlo, and some brown leather Sperry’s.

Eshan Shah

Business Development Manager

Denim Jacket: Zara


There are few things that are as comfortable to throw on as a worn in jean jacket. Granted, my distressed denim was only recently purchased from Zara, so all of its character is artificial (but hey, that’s just another thing we share in common). The intended illusion is one of laidback comfort, as if this jacket has experienced years of travel. Plus, this type of ‘weathered’ jean jacket is incredibly soft, and its suppleness suits the boho-chic vibes of my lacefront Vera Moda tee. The choice of a lighter wash often reads as more casual, and to me, the neutrals and lighter colourways embrace summer vibes. I kept these lighter tones consistent from my jacket to my shoes, which leads to some disputable denim advice, dress like your favourite insta-filter. The answer to that is Buenos Aires of course.

Jonathan Cavaliere

Creative director

Denim Jacket: Levis Tailor Shop


Let's get this out in the air. I love denim jackets. I might have 8 different variations sitting in my closet right now. I’ve got everything from a shearling trucker jacket (as seen here), to a double-breasted indigo denim blazer (as seen here), and everything in between. That's why when Levis reached out to create my own denim jacket at their tailor shop, I was pretty enthusiastic to say the least.Outside of being a self-proclaimed denim head, I really wanted to create a piece that I could travel with. As a proud Canadian, I wanted to bring the very fabric of our country with me wherever I jet off to. So, I worked with Maria Stoop to create a piece that was as much a Canuck as the Canadian tuxedo. We took a piece of the Canada 150th leaf logo and made it peak out from the shoulder seam. To represent the 6 (I never thought I would actually reference Toronto with that, thanks Drake), we did a silhouette of the Toronto skyline on the back of the jacket. For obvious reasons, this piece has becoming my personal favorite and one of my carry-on essentials.