Who are you wearing? What’s the latest trend? Where am I wearing this? Relevant questions, certainly. But of all the dilemmas facing the modern-day fashion consumer, it’s the “when’s” that turn usually confident, self-assured people into self-conscious ditherers.

1. When should I adopt a trend?
“Before the curve. If you see it on anyone from The Hills or Britney Spears or featured in InStyle or any of those tabloids, forget it. It’s so done. Unless of course, it’s on Rihanna or Gwen Stefani, who are always ahead of the pack.” — Georgia Groom, wardrobe stylist.

2. When is it too late (or too early) to wear white? Do Labour Day rules apply?
“That rule is meant to be broken. Chanel made the white tweed suit a perennial year-round. Also just look at the white shirt or ski wear: White today is seasonless.

“White has also entered the new world of social consciousness and sustainability — non-coloured organic cotton in natural and unbleached fabrics. White will become the new black.” — Barbara Atkin, vice-president of fashion direction, Holt Renfrew.

3. At what age should a woman cut her hair short?
“It depends on the individual, the type of hair, whether it changes with age, her career and lifestyle. The length of hair is not dictated by age. That's so old school.” — Ivan Gibski, hairstylist and director of Flaunt Boutique

4. When should a man buy his first good suit?
“Men shouldn’t wait until there's an occasion like a wedding or a prom. They should have one in their closet. The day they decide they want to make a good impression is the day they should buy a good suit.” — Melissa Austria, owner of Gotstyle menswear boutique.

5. When is a girl old enough to wear makeup?
“Whenever she is comfortable and expresses an interest. My daughter and her friends in high school experiment mostly with a little lipgloss, eyeliner and concealer when they get breakouts.” — Susie Sheffman, fashion director of Fashion magazine.

6. When should a woman stop wearing open-toed shoes?
“We as Canadians try to drag summer out, but by the end of September, it’s time to get into boots.”­ — Stuart Rice, marketing director, Browns.

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