Today I can verify all of the shopping advice given here is true, that is being calm, acting confident and look like you belong there.
I went this afternoon to Shoppers Drug Mart, told a SA in the makeup area that I had nothing and needed everything to get started.
Off we went picking up stuff I'd need, got colour matched for the concealer and foundation right there.
The biggest thing is that no one cared, some dude* in the makeup area? All the other girls there were busy doing their own thing.
I left there $200 lighter, but a lot more confident which is why I'm posting this thread.
Hopefully some people will read this positive story and gets inspired to try it for themselves.
Note: I believe this is the correct section, it's not about what I bought but more the story about how no one cares what you do.