The photos from Toronto Life’s Best Dressed party at the Trump Hotel indicate two very important things: 1) fashion should be fun, 2) there’s absolutely no need to be intimidated by Toronto’s best dressed. (Photos also illustrate that the midriff is having a moment.)

I was supposed to attend the event last Thursday, but after a busy day, I didn’t feel like I could pull myself together in a way that would be appropriate for the city’s most stylish soirée. Now, looking at the pictures, I’m realizing that I could have worn any of the following: my housecoat, the zip-up outfit I have worn to paint the living room, my leather jacket and the brightest lipstick I own, a crop top and whatever, any dress in my closet.

It’s not what you wear but how you wear it. I know this, I’ve known this for a long time. Still, sometimes it’s easy to get intimidated by “the most stylish,” but really we’re all just playing dress up the same way we did back in kindergarten. Be playful & enjoy.

Toronto Life’s Stylebook is now available for purchase.

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