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I suggest this hat:

 

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My current parka says Goose Down Duvet D'oie and the buttons say Retreat. That jacket could be too warm for Montreal, but it depends how you tolerate the cold. Montreal and Toronto tend to be wet and miserable, so you need to be dry. This jacket might not be dry enough.

The best deal I ever got on a jacket was in Calgary, a Sun Ice ski parka. The ski fasions change all the time from drab to colourful and back, so this was the previous year's model. It was relatively light, as warm and dry as could be, extremely tough, durable and less than a third of the original price.

The coonskin cap would certainly set you apart, and maybe get you splashed with blood.
 

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Your boots should have a lot of grip. It can get deadly icy in hilly Montreal, you fall and break your hip or your wrists. Learn to shuffle along safely. Snow is grippier than ice most of the time, unless it is fresh powder on top of ice. They make some great shoes in Montreal.
 

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For boots I love my Merrill's. Super warm, nice and grippy, and durable; I've put 1000km on my current pair and they're just like new.
Do they come with an odometer?
 

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Your boots should have a lot of grip. It can get deadly icy in hilly Montreal, you fall and break your hip or your wrists. Learn to shuffle along safely. Snow is grippier than ice most of the time, unless it is fresh powder on top of ice. They make some great shoes in Montreal.
Yeah shuffle on ice and keep your hands out of your pockets. If you go ass over tea kettle, you’ll need them to try and catch yourself.
 

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Looks cool, but, one has to deal with PETA.
Also, doesn't protect your ear lobes.
PETA is an affront to the entire Acadian way of life 😎
 

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Back to guitar talk…
Kijiji.ca
Specifically kijiji Ottawa. 😆

This is a bit of an inside joke but sort of not. We have a section on the forum called “Kijiji Alerts”. Kijiji is an online classifieds site similar to Craigslist or Facebook Marketplace. People will post links to any good deals they see (that they don’t snap up for themselves). The running joke is that all the best deals always seem to be in Ottawa. Luckily, it’s only about a 90 minute drive from Montreal.

The other thing you’ll see is that some sellers in Montreal can be a bit “ambitious” with their prices. For example, a US Strat might sell in the $1200 to $1300 range. In Montreal, they’ll list it for $1700, drop it to $1600 a month later, then up to $1800 for the next 2 months.

 

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Like some have mentioned, Kijiji and facebook. I noticed that there are lots of great deals posted in Quebec and I always wish I lived closer to take advantage of those.
Absolutely. It seems like the Montreal area is the place to get the best gear. Theyve got all the best inventory at the big stores(L&M, Steves, the other one) and numerous small shops and boutique sellers, like Lauzon and ElectricMojo. Theres loads of good deaps on Kijiji, and theyre fairly close to Ottawa that doesn't seem too far behind in terms of deals and shops.
 

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I live in the Ottawa-Gatineau area, which is comparable to Montreal climate-wise (but with much less traffic!) and I'm out walking my dogs 3 times a day, year round. I would recommend a layered approach to dressing for Canadian weather. Although I have coats for every conceivable weather event, what sees me through 95% of my travels is a wind/water resistant outer shell combined with one of several fleece jackets of varying weight. Under that combine layers of shirts, t-shirts or sweaters to taste given the weather conditions. Always a good idea to start with a moisture-wicking base layer against your skin as well... for both torso and legs.
 

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Welcome ImIago! I have a number of friends from South Africa who have moved to Canada for various reasons. Montreal is a very diverse city so you should find fitting in not overly difficult. If you speak French that will help but there are areas that are more English speaking. I would keep that in mind when you move. Google is your friend for finding those areas and finding some unique music shops. There are some good deals south of the border where you can have gear shipped to a border town and go over and pick it up. Shipping is often free in the USA to most of their states. The US border is only about an hour from Montreal.
 

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Welcome to Canada! And just as others are recommending places to buy vintage gear, you can find excellent winter coats at vintage stores in Montreal, too. I would never pay $1500 for a new Goose coat, but a few hundred for a gently-used one is totally reasonable.
 
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