Year after year, I complain until my friends’ ears bleed about the crappy polyester slutty (insert a profession/object here) costumes that invade the streets of Toronto on Halloween. And this year is no different. I am sure the parties and clubs will be full of nurses, cops, flight attendants, etc. in cheap flammable outfits, and once again I will be wearing something that I pulled out of my own closet.

This year, I wanted to wear a costume that had something to do with fashion…avoiding the usual cliches of donning the “Anna” wig, the “Audrey” LBD, or something else equally predictable. And then, last weekend, while browsing the Halloween section at the Blue Banana, the inspiration came…in shape of a fake beard. My mind immediately went to the now infamous Toronto Life editor – Kevin Naulls. “Why hasn’t anyone else thought of dressing up as Toronto fashion notables?” – I thought. This city is full of vibrant characters equally as intriguing as Mr Lagerfeld, and Ms Wintour…or at least interesting enough to Toronto folks. And so this post was born.

If you’re not from Toronto, you might not be familiar with some of the people below…but I am sure you can conjure up costumes of your local fashion superstars too. All it takes is a little imagination.

1. Jeanne Beker – Fashion Television Host

Is there a person more recognizable in Canadian fashion than Jeanne Beker? I don’t think so. Jeanne Beker is an institution. And as such, she’s an easy target for Halloween costuming (is that a word?). Her costume is actually super easy to put together. If you aren’t blessed with a dark brown mane like Jeanne’s, pick up a wig with her signature blunt bangs. Grab a black shift dress (perhaps from her EDIT collection at The Bay?), cinch it with a cool belt (she wears one with a dinosaur buckle), pair with sky-high black pumps, grab a mic, and you’re ready to go find yourself in fashion!

2. Kevin Naulls – Toronto Life Online Editor

Main source of inspiration for this post, and a man that makes socialites tremble with fear and/or anger at his sometimes cutting, always hillarious photo captions. All you need to be Mr Naulls for a night is a good fake beard, something plaid (shirt, trench, scarf – use your imagination, people!), fun socks that he’s often spotted wearing, and a copy of Toronto Life in hand. Kevin, is that you?

3. Anita Clarke – Blogger

Bloggers are a huge trend, they say…and a trend that won’t be going away any time soon (we hope). And what blogger is more fun to emulate than Anita? My favorite (and most Halloween-appropriate) look of Anita’s of late was her fab Mark Fast jumpsuit – part catwoman, part fashion superhero, if you’ve got the body to rock it, then, I say, go for it! Don’t forget an awesome pair of shades, and a pair of Dean Davidson earrings to complete the look. Meow!

4. Sarah Nicole Prickett – Writer

SNP’s raw and insightful writing is the reason we tune in to her personal blog week after week. But it’s her killer style that makes us think she’d be so fun to wear for Halloween (err…not literally, of course). If imitation is a sincerest form of flattery, flatter her by wearing a rad pair of wedges (straps, peep toes, stripes…), tee off your boyfriend’s back, leather skirt layered over another skirt, and a swipe of red lipstick.

Finish the look with a tousled blonde wig (that you can trim to make it look slightly uneven). Use pink (or purple) highlighter to give the wig some fun highlights. And though we’ve seen SNP smile many a time, your costume won’t be complete without her signature smirk.

5. Kirk Pickersgill and Stephen Wong – Designers of Greta Constantine

We see this designer duo everywhere! At industry parties, product launches…and of course, at their very own fashion shows. And their unmistakable style makes them perfect costume material! If you are looking to dress up with a friend – this is a great costume idea for you! Both Kirk and Stephen wear a lot of their own designs, so definitely go for something flowy and layered, in shades of black, white, and grey (leather shorts for Kirk, sweat pants for Stephen). Wear a pair of aviator glasses as Stephen, and thick black rims as Kirk. For Kirk’s outfit, you might want to find a paperboy hat similar to the ones he likes to wear, and for Stephen’s topper, choose a trucker hat, or just wear your hair in a knot on top of your head.

Hope you enjoyed this costume post. What other Canadian celebs Halloween costumes would you like to see? Share in the comments!