Plan on passing through an airport a few times in the next month? First let me say, I'm sorry. Secondly, let me tell you what to wear so that at the very least you'll be (worse case scenario) delayed in style.
Base of this look is the Canadian tuxedo, of course. Start with your favorite dark wash skinnies and worn-in denim button down. Throw a cute oversized sweatshirt over to stay warm and cozy in the cold a/c. Wear flats to breeze through the security checkpoints STAT. Early morning flight you just barely made? Wrap hair in a low bun and top with a cute hat to hide bedhead. Ran out the door sans-makeup? Spritz some refreshing mineral water and slide on a pair of dark sunnies because honestly, they're lucky your eyes are even open at this hour. Still cold? Bring a simple, asymmetrical-button wool coat that looks good left unbuttoned over your outfit. Tie it all together with a carry-on duffle filled with in flight necessities (tabloids, gum, eye mask, pills, makeup, ipad.)
Cute, comfy and ready for post-flight shenanigans. Hopefully your travels are as painless as your outfit.