Does glamour have to be grim: thinking about the cruelty of chic...

In June of 2006, I encountered the chicest woman I have ever met. I can’t say for sure if she was tall, but I remember distinctly that her heels were. She wore sharply pointed slingbacks—no cutesy peep toes for her—that easily could have been used to gouge out the eyes of anyone who looked at her the wrong way.

She walked in with a big snakeskin purse and an even bigger reputation for being indomitable and sharp-tongued. She was a national broadcaster from Toronto—and still is—so let’s call her Isabella.

Read more of JJ's story, "Do you have to be cruel to be chic," in the latest issue of ELLE Canada.