Focusing on utility – The Keep Pursuing messenger bag

The focal point of today’s outfit revolves around the super functional bag by Keep Pursuing. Regardless of what you’re wearing, this bag will compliment the look. At first glance, it looks like your average, casual messenger bag. But it has a generous amount of space to carry what you need for a whole day – regardless of what it is you find yourself doing. The bag initially contains large basic compartments, but offers the option of interchangeable add-on’s that you can change based on your needs! In all honesty, I thought the bag would not fit my wardrobe choices, but even with a layered look, the bag manages to fit in. They have a variety of other bags in different colors and styles, but I thought this Face Off bag + Utility flap would work best for my style choices. Definitely worth checking out if you find yourself wanting to carry your daily needs in one bag!

Moving forward to the outfit now!

I chose to wear a layered look instead of throwing on a large parka. Despite the Toronto weather, it was warm enough and comfortable as well – not to mention, more stylish and exciting than throwing on a big coat. This is a very functional look that can carry you through a long winter day. Get too warm indoors? Take off a layer.

The bottom most layer is a linen gingham shirt. Simple and comfortable shirt, as well as a pattern that is easy to work with! I layered that with a surplus military jacket that was thrifted for a mere $10. Adds character to the outfit while keeping you sufficiently warm. A quilted vest over top of all that showcases the details of the garments underneath while adding more personality to the overall outfit. Beyond that, you really can’t go wrong with whatever pants you wear with an outfit like this. I kept it simple with grey jeans. As for the shoes, boots are a more logical choice – however I decided to focus more on style with this funky oxford – but wear whatever is comfortable for you in the winter!

I also want to thank Reeny once again for the photography! Made all the pictures turn out great in today’s snowstorm! Truly thankful for all my amazing and talented friends.

Thanks for reading fellas! Stay warm and stylish!


Linen Shirt: Club Monaco

Military Jacket: Thrifted (You can find similar ones in Kensington Market in Toronto)

Quilted Vest: Club Monaco

Jeans: Uniqlo

Socks: Club Monaco

Beanie: Wal-Mart (Honestly, it was nice for the price)

Oxfords: Aldo






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  1. Love the vest. The layered look you did here is a great as an alternative option to wearing a coat! Sometimes a coat can really throw off an outfit, especially if it doesn’t really go with what you have on at the moment. The blue vest with the green underneath is a nice contrast!

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