I just bought this killer dress from Killstar, it's prob my fave right now. I also like the stuff I have for my Concert Blacks (what I wear onstage for orchestra) - I have sort of a black cardigan, then a a sleeveless black tunic dress and some leggings. It definitely feels like a "power outfit" for me.
As for being trans in Canada vs. the States, It's very much about where you live. Canada is of course generally more safe because of trans protections,some of which are still being passed through legislation. If I was beaten for being trans it would be considered a hate crime here, unlike in some parts of the US.
Having said that I would feel more comfortably being visibly trans in a Metropolitan American city than I would in small town Saskatchewan or Alberta (no offence Alberta. Full offence, Saskatchewan). Being trans and out can be dangerous everywhere, though, especially if one doesn't "pass" (defined elsewhere). It can be hard to get work, old workplaces can become toxic. There's a reason so many trans women, especially trans women of colour are in sex work - Sometimes it's the only work that will have them. But that means being a person in danger in an even more dangerous line of work (due to laws around sex work but that's a convo for another time) - it can be a deadly way to live. 7 trans women have been reported murdered in America so far this year, all of them women of colour. If I remember correctly, someone worked it out a few years ago as trans women of colour having a 1 in 8 chance of ending up murdered - I couldn't cite a source on that, but considering their percentage of population they certainly do get murdered a lot.