Just recently I was sent on a job to evaluate customer service levels of a few stores. I went into the stores as a customer. Since I had to evaluate 7 stores in the downtown area, I dressed comfortably. By that, I was in decent track pants, and running shoes, in my sporty jacket, had light make up on. Here's a picture of my shoes.
Nevertheless, it was a funny experience, because the area I was in, was the downtown financial district. 90% of the population had a suit on - since suits made a come back in the last 2-3 years, bouncing back from business casual. The message most of these people sent were: we are doing serious business in a serious place. We have no time to waste. And here I am, bobbing up and down the streets, in my shoes that someone had described "that had the color of a highlighter". I received many stares, not of hostility, but of interest.
This may not happen in a place where people's dress codes are less homogenous. But to fit into Toronto's downtown financial district, it's best to have a suit on.
By the way, I think they were jealous of the free spirited-ness that I radiated, since they could not afford to be this way because of their jobs!
