During the transitioning seasons in Toronto, you never know what’s going to hit you. Sun, snow, heat, hail — these are all things we’ve had to endure from day to day over the past few weeks, making it incredibly frustrating to get dressed in the morning.

When battling the elements, I can’t think of anything better to wear than a trusty army jacket. It’s durable, warm and can provide the perfect amount of protection and comfort whether the temperatures are high or low. This particular jacket was found at one of my favourite vintage stores in the city – Pretty Freedom – in Kensington Market. I still can’t decide if I was more excited about finding the jacket or the old school Club Monaco button that the owner pinned on me to go with it. From shielding me from a (near) hurricane in Brooklyn to acting as a park blanket when the sun was out, I don’t know how I would have survived the past few weeks without this jacket.

In fact, this entire look was put together to prep for any weather and any situation I might face. The bag? Big enough to hold a pair of flat shoes, an umbrella and a cardigan (in case the weather turned). You already know how I feel about the jacket, but in this case it also made my Helmut Lang top and leather-look pants more daytime appropriate. However, I would easily be ready for dinner and drinks with it off.

When I leave my house in the morning, its hard to know where my day will end up taking me, so I dress to be prepared for anything that comes my way.

What I Wore: Vintage army jacket from Pretty Freedom, black cut-out sports bra by MICHI, draped chiffon top by Helmut Lang from Fashionably Yours, pleather pants by Graham & Spencer from Fashionably Yours, bag from Roots, shoes from Aldo.

All photos by Steven Lee of Silhouetted Skyline