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T was born in March in the PNW. I'll be honest. I overbought. It's no big deal to grab a few extra items on an as needed basis- unless you don't have a washer/dryer at home. It is a big deal to to to manage all the stuff.

Do buy newborn- but only wash a few items. Leave the tags on the rest just in case. T was almost 8 lbs and in NB 2 months.

I vote get a week of clothes for NB, 0-3, 3-6. You will get gifts. Then 3-4 pairs of pajamas. I liked my girl in daytime and nighttime clothes- if you don't care just a bunch of footie sleepers is fine.

Long sleeve onesies were my favorite. Get pants with feet already on them so you don't have to struggle with socks. Hanna Andersson has the best socks that stay on- also cotton pilot caps. No sure if you have it in Canada.

I have three Canadian winter babies.

1 nb size sleeper (was worn once by one child)
10 0-3 mo size sleepers (we always did cotton in the early days. I find fleece doesn't breathe enough for newborns. I prefer snaps until four months and then zippers. Bonds makes great zips that go top to bottom and bottom to top loved those, they also make long sleeve zip sleeping bags. If I was starting over I'd use those exclusively. Wrestling with newborn legs in the cold at night is no fun.)
4-5 long sleeve onesies
2 fleece/wool/warm cardigans
4-5 pairs of leggings, sweatpants... Cosy stuff
Two pairs Zutano or Padraig booties
6 pairs if cotton socks
One fleece hat
One bunting bag for stroller (I have JJ Cole Arctics)
One car seat cover
A couple wool or fleece blankets
A set of A&A blankets

We never did snow suits before the first birthday. Keeling then bundled in a car seat/stroller is easier. Also didn't do mittens just tucked hands in to jammie sleeves.

Our pediatrician advised against polyester fleece, instead advocating for natural materials (cotton). Said some babies are sensitive to synthetics, and that they can make it harder for baby to regulate its own temp. We also do a lot of merino wool: wool sleep sacks, wool onesies under cotton when its very cold, wool hats. We do use polyester "snowsuits" (Zutano, patagonia, l.l. bean) for things like hiking outside.

@oliviaoblivia posted a great list. I would start there!

Ultimately, it's actually sort of tough to figure out, because you don't know how big your baby will be, how long they will stay in each size, or how much people will give you. Especially being due near the holidays, I imagine you will receive even more stuff than usual from family and friends. Definitely buy close to your due date and keep tags on many things. It's really easy to overbuy (especially in the tiny sizes).

As you know, I'm expecting a Dec baby too and this time around, I will probably focus on getting maybe 3-5 cotton sleepers in sizes NB and 0-3, plus some baby mittens, socks, some new swaddles, and a car seat cover (somehow, we never used one for my Oct baby).

With my LO, I discovered that my family and friends LOVED to give us: tiny multi-piece outfits (but not necessarily sleepers), bunting (we got 5!), and a million hats. So I probably won't buy any of those at all. They all forgot things like mittens.

I had a semi-preemie in winter in NY so I really had to bundle him up! Honestly, all the kid wore were fleecy sleepers with feet. All day and night. Getting him into things like socks or god forbid those silly baby pants was pure torture. Any separates (ie shirts/ sweaters) ride up and will expose his cold tummy. You can't take them out for a few weeks anyway so make your life easy and get those zippered sleeping onesies!!

Agree with footed sleepers. My son was almost exclusively in those for the first 3-ish months.

And second the zutano booties. They are warm for outside travel and can't be pulled/kicked off.
I don't think I had fleece until he was a little older, but we did have some cotton terry cloth sleepers from Carters and they seemed a little warmer than the standard cotton ones.

Also, it's not clothing, but I love using the rain guard for my stroller and carseat in the winter. I see lots of other city moms do it too. It helps shield the bitter cold wind and keeps some of their heat inside.

If you're going to be outside, pushing the stroller at all, I highly recommend getting a stroller hand muff.

My winter baby lived in fleece sleepers until spring. I probably had 5-7 in each size so I didn't have to do laundry every day. Also soft pants and long sleeved onesies. I didn't really do hats, but I also used the "bad" bundleme. It doesn't get super cold for long here though. .

Oh and zutano booties are a must!!

Yes, the zutano booties as pp mentioned!