To be honest, I’m a bit of a Halloween hater and despise getting dressed up. Yes, I love to dress up on the daily (in “normal” clothing), but I’ve never seen the point in spending money on a costume when I could spend money on a new outfit. So as you can imagine, I tend to put any costume planning, sourcing or buying at the bottom of my list, often resulting in last minute “What the F**K am I going to wear!?” moments.

While I’ve got a couple of ideas in my head for this weekend’s costume-filled soirees (more on this below), StyleBlog.ca had me laughing out loud when I stumbled upon her suggestion of dressing up as Toronto Fashion Heroes. Instead of the usual, globally recognised and “predictable” fashion figure costumes – Anna Wintour, Karl Lagerfeld, Audrey Hepburn – StyleBlog asks: “Why hasn’t anyone else thought of dressing up as Toronto fashion notables?”

So she came up with a list of the city’s most “vibrant characters” of the fashion industry that includes: Jeanne Beker, Kevin Naulls of Toronto Life, blogger Anita Clarke, writer Sarah Nicole Prickett and designers Kirk and Stephen of Greta Constantine. Providing a description and ‘How To’ instructions on how to easily achieve their signature looks – and they’re good!

Examples below and full post HERE.

How To: Sarah Nicole Prickett

How To: Kirk & Stephen

Now back to me and my costume woes. While drunkenly chatting away with Plaid Magazine editor, Odessa, at JMC’s SS12 presentation a couple of weeks ago, she revealed that she was planning on dressing up as Cher Horowitz for Halloween. This got me all kinds of excited and I told her that we should take it one step further by going as the Clueless CREW – I would be Tai and my bestie, Rachie Baby, would be Dionne – perfect! Now, if you know me well, you’re probably wondering how the hell I was ok with being Tai instead of Cher, so, let me tell you that Odessa was wearing a wide-brimmed mink fur hat during this conversation (and she is also blonde) so she won the coveted spot, hands down.

But last night Odessa texted me with costume woes of her own – a hole in her Cher top and no mini backpack or thigh highs! So she has graciously passed on the Cher torch to me as she is now going to be a famous musician, but I’m obvi not going to tell you who – don’t want to ruin the surprise! Now it’s down to me and Rachie baby to source some last minute faux fur, pastel tartan and brick phones. Will we be successful in our Saturday morning challenge? I’m not sure. So if all else fails I’m going as…

Courtney Shane! Yep, Lady Shane in this particular scene, to be exact. Slutty much? I know right. But let me walk you through my reasoning. I recently purchased this rather garish bright blue vintage nighty from Salvation Army, and I figure if I cut it real short it could be quite 90s and Jawbreaker-esque. Glossy lips, hair in pigtails and a phallic-looking popsicle in hand and I’m in business! Hopefully I won’t actually be offered er, “work” while walking down the street in this.

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And if this doesn’t work out either I guess I could just throw on a black dress and grab a microphone (from somewhere?) and be Jeanne Beker! Wish me luck.