Yesterday I went to a local fashion consultant, Wear2Start.
They are a Victoria based non-profit that helps women of all types find clothing, ostensibly for the workplace, that fits.
It was a great experience, they were very enthusiastic, and gave me many choices, including some really nice boots, a winter jacket, and several outfits. They even gave me a bra and some breast forms.
Any trans (or cis) woman who wants help getting started on a classy style, I would highly recommend calling to set up an appointment.