StyleJonathan Cavaliere

Back to School Style

StyleJonathan Cavaliere

Back to School Style

Even as an adult, there is something about September that always makes me feel like I’m going back to school.

I get those anxious feelings that summer fun is over and the next couple months will be filled with exams and essays (or in my case, lots of work!)


To my parent’s dismay, the days before school weren’t spent at the business depot; instead, I was interested in visiting the mall. It was a place where I could think about the year ahead and how my clothes would inform my classmates of the new-and-improved me.

I would walk into stores and try on some of the freshest clothes to see if it felt right. It was all about wearing the coolest gear, but adding an element or two that really stood out. In the spirit of back to school, I thought I would put together an outfit with help from my friends at Upper Canada that even the teachers would give an A+.


As a jock in high school, I have always loved clothing that is tied to heritage sporting items. This green bomber jacket from the Gaphas an inherent military vibe, but also resembles a classic varsity jacket.

I think all guys should own a classic grey t-shirt. This one from Zara fits great and it’s the perfect piece to just throw on when you’re running late for class. When it comes to jeans, comfort was key for my athletic thighs and for that reason I picked up a pair of Paige denim at Strauss Menswear. Chelsea boots are a great footwear option for any guy who wants to elevate a casual look. For this reason, I decided to pick up these suede Chelsea boots from Stance.


Last, but not least, is your backpack. In my opinion, a backpack is where you can really have fun and add some personality. This blue floral version from Stance has all kinds of compartments for your textbooks - and it’s also a great way to stand out in the hallways.For more great back to school gear, head over to Upper Canada!

Words by Jonathan Cavaliere

Photography by Steven Lee