Looking for Toronto, Canada appropriate fall clothing.

Recommendations? Deals going on (we do have our bike show fall clearance next week)

Expensive, But you will never regret it, cool when warm, warm when cool, warm even when wet.
https://shop.ibex.com/Apparel/Mens-Ri...-Sleeve-Jersey

This is what I wear:

14-17°C arm warmers
10-14°C arm warmers,knee warmers, full finger gloves, maybe vest
7-10°C arm warmers,knee warmers, full finger gloves, jacket, merino base layer
0-7°C winter jacket, winter gloves, merino base layer, skull cap, tights

Pretty similar for me, except subtract 5 C for each.

Every Ibex piece I have is superb.

I would second this. I have an Earth, Wind and Rider merino jacket with a hood (not a big floppy hood, but one that you can fit under a helmet), and it's a favorite on or off the bike. One of my favorite cycling-related purchases, ever.

Same here, but subtract 30 C for each, and it's a blizzard and every street I ride on is uphill. HTFU.

(Kidding, kidding!)

When the team changed their kit I had to think about what I wanted to buy. This is what I got, in this order:

1. Jacket (warm, not just wind resistant but also insulating). This one the sleeves zip off.
2. Wind vest
3. Long sleeve jersey (after getting 3 or 4 sets bib shorts and jerseys, plus arm warmers which I almost never use, plus lycra shoe covers)

I have shoe covers (lycra, knit sock-like covers, and finally insulated booties), long finger gloves (summer and winter - I always wear them, even in summer), and head covers (thin or thick lycra type).

Finally the key for me are 3/4 shorts aka knickers. I have them in the "roubaix" fabric (brushed on the inside so it's a bit more fuzzy, more insulating, wicks moisture away). I have a bunch of those as I wear them from 35-55 deg F, and I rarely ride outside below 35 deg F. Knickers are especially good when it's raining out because they don't get as heavy as tights, and wet they're both about as effective in keeping me warm. Shorts in the cold rain exposes the knee to wind and so it's just a bit too cold.

I find knee warmers leave the (ahem) upper parts cold. A teammate bought some winter weight bib shorts but I haven't heard reports from him. The theory is to combine those with knee warmers to get a modular version of the knickers I have. I can't get team shorts in winter weight so for now I'll stick with the knickers since I have 4-5 pair of current ones.

Keep your torso, hands and feet warm. At 55 deg I'm in shorts but with booties, long sleeve top, wind vest, long gloves, head cover. I prefer some coolness on my arms/legs and a very warm torso.

Here's one very much like it, but on sale:

https://www.backcountry.com/ibex-shak-t-neck-jersey-mens

This is my merino base layer:
https://www.mec.ca/AST/ShopMEC/MensCl...eneck-mens.jsp

There is a Fall season in Toronto? I thought there are only two seasons there: August and Winter

Seriously though, I don't think you need to over think this. Just get a wind vest (any will do), full finger gloves, and a pair of arm warmers (wool would be best), you are set. The single most useful piece of cool/cold weather cycyling gear I have is a neck gator. It works wonders, and I would suggest you take a look. With that, you can ride into the low single digits.

Do you all wear shorts / bibs throughout the fall?

I wear and love these, too. When it gets cold, I use leg warmers for my ankles. The knickers are just short enough not to get caught in the chain. They're great for hiking, too.

I'm an under armor guy through and through

WTH?

https://www.probikekit.com/us/clothing/cycling-clothing/cycling-jerseys/castelli-trasparente-due-wind-fz-cycling-jersey-1032781.html

^^^ it keeps you very warm.

!5,000 dollars is a bit steep for a jersey though.

What? I have 3'of those, I use them as a liner in my bird cage.

It's lined with down from griffin hatchlings - great insulator, no bulk.

Which sounds like a good idea when you fall.

That should do it. Add blue scarf for additional warmth.

What a horrible team; plus they're in lock out!

Your thinking of over armour, that's for falling. Under armour tends to shred on impact haha but atleast it's 1/3 the cost of wool.

I have no love for the Leafs, except that they're one of the original six, their uniform is classic, and they've won numerous Stanley Cups. I just suggested it because the OP is from Toronto, and presumably likes them...

My local team has never won a Cup, so I don't throw stones.