Well, snow boots will probably be a bit overkill -- they clear the sidewalks and the streets here, so unless you're walking through a park, you can get by with something smaller. Of course, if it's horrible out and things have warmed up, we can get puddles of slush at the corners, in which case something waterproof is very nice, but I actually get by all winter with just some slip-on insulated shoes.

In most restaurants and stores and such, most people just wear their boots, unless it's a fancy going-out kinda place, in which case women will bring shoes in a small bag to match their outfit, some men do, but hardly as often. In people's homes and in offices and clubs, you change out of of your boots into shoes.

If you're going out somewhere where you've dressed up enough to have matching shoes, you probably want to take a taxi :)

Agree with josee. Most women in Canada own multiple pairs of boots that range from practical, heavy duty to beautiful and impractical ... and everything in between. However as a traveler and possibly not someone who owns as many pairs/not from a climate such as ours, then bring the ones most suited to your main activities in the city and change into your shoes for a more dressy evening. The key is to have the boots that will keep your feet the driest and warmest. Don't overthink it and don't worry about what other people think.

More of a question of if you want to wear your boots all evening long. In restaurants, as written above, most of times the ladies will bring a pair of shoes in a shoe bag and change footwear at the cloakroom. Some will dispense with the shoebag business if they are sure that it will be almost door to door.

Clubbing is different as the hustle and bustle around is not fit to spend a long time at the cloakroom. For example some clubs and bars have some ponchos on hand at the entrance so that smokers don't have to use cloakroom all the time when they go out for a coffin nail. So then the need of door to door transportation will be greater and, for visitors, easy to get by cab. Otherwise be prepared to spend a full night in your boots and with the sweat and everything it might be incomfortable after a few hours, unless using some trendy boots and booties that are ok for being worn for long periods. but usuallynot so well insulated and even less waterproofed.

You know Jen it is not such a silly question and for regular DE it can come as a refreshing query that will make for a change from the usual question about how to come into town from the airport.

Didn't see that Phpr had answered too. I assume that this a female contributor that has a perspective of a women as Tristou and I are gay male so we couldn't really grasp about the many pair of boots that a woman can have., We, gentleman, will make do with may be two pairs or even none in Tristou's case! lol.

Rickb: although boots are much easier for men it's true -- basically, black or brown sums it up -- I'm not so sure I'd start a fashion war pitting women and their footwear against gay men and theirs. Why even I -- hardly the fashionista -- have a pair of bright red shiny leather boots. They're ankle-high, completely impractical, not waterproof nor particularly warm. But at least I can say that yes, I do have a pair of boots, and smashing ones at that :)

I love my shiney red Blundstones. Wear them all over the place for dinner.

For very posh places I just take a pair of heels and change. But I try to avoid those places!!

Just pretend you are going out for a night of dancing with a snowstorm out there. You would wear your boots to get there and then change in your dancing shoes when you got in the door (cloak room) and when you leave you would retrieve you boots and put your shoes in the bag.

But then again if you want to entertain just walk out in your high heel dancing shoes on the slippery sidewalk.

I have swims overshoes. They are waterproof and stylish.

Oh no! A platypus wearing galoshes!