The weather has taken a serious dip in temperature recently. Yesterday was bad and today was downright unreasonable.

Normally, I would just hang up the bike and call it a done commenting season, but this year:

1) the weather has turned cold way to early
2) I'd like to continue biking for as long as I can before the snow comes.

I need to buy some clothing, but wanted to see if anyone had any advice/suggestions/best practices for low cost/proper/comfortable options. Any advice, as always, will be appreciated.

Go to MEC and check out their cycling clothing. MEC branded stuff tends to be reasonably priced.

Luckily, I didn't have to buy anything special when the weather turned cold last year--I've obtained quite a collection of UnderArmor products from my soccer days, and they were more than enough. I often got to work sweatier than in June. My general ensemble:

Torso (order from bottom to top):

L/S Underarmor cold gear mock turtleneck
T-shirt
(if really cold, a thin wool sweater)
Fleece pullover (also a relic from my soccer days, it's made by addidas, fleece inside, weatherproof shell).

Legs:

Underarmor cold gear soccer socks
Underarmor cold gear compression shorts
long johns
Wool socks

That get-up was great. I can't remember ever feeling cold, unless there was a lot of wet snow and my feet got soaked. From what I understand, Chicago and Toronto have pretty similar climates, so that should work.

Remember that you don't necessarily have to go with cycling specific gear. Sure it does the job and is designed for on the bike fit, but it'll probably be a lot pricier and won't do much better than cold weather athletic gear. Think about sports that play outdoors in rough weather (soccer, american football, and lacrosse come to mind) and see what kind of products are offered for those sports by Nike, Adidas, Underarmor, etc.

Wool layers.

Layers are your friend. Merino wool is your lover.

snowmobile helmet, ski pants, windbreaker jacket and Nike jacket underneath (with the kind of material that dries quickly), hiking boots

cheap Canadian Tire bicycles can last more than 2 winters outside.

Are you joking or what ? I live in the suburbs of Toronto, it was only 50 F or 10 degreess celsius. No need for any special winter clothes at those temps. I love those temps, perfect for riding.

Getting all bundled up to go biking doesn't work for me. I'll put on a single layer cycling specific jacket, headband, & insulated gloves for temperatures between 30 & 40F (~0-5C). Colder than that, too many compromises for me to enjoy the ride.

This post made my day. (see signature)

OP, check out the Winter Forum -- lots of threads on winter wear.

And by the way, no need to quit just because it snows.

I live in Toronto and tonight's ride was chilly from the wind. I wore bike tights, MTN bike shorts over those, a long sleeve jersey and a windproof jacket as well as a pair of thin gloves. This get up will last me until January when I swap the thin jersey for a thicker jersey and replace the MTN bike shorts for warmer windproof pants as well as winter boots, a ski helmet and heavier winter gloves. For extra drama I have a nice neoprene face mask and ski goggles when the word "windchill" makes me twitch.

This winter I plan on buying studded snow tires so I don't fear icy rides any longer AND get to ride like a maniac on the ice covered Beltline trail!!

Yeah, baby!

But be careful on those studs. You are probably kidding but in case you are not, realize that you can't really get away with riding like a maniac on them.

Although not a clothing item, ensure that you have plenty of safety lighting/reflectors, etc given that the sun does not rise as early. Even at the end of my rides in to work (I live 4hrs drive north of Toronto), arriving at about 7:15, although there is plenty of light in the sky, the sun hasn't yet crested the surrounding hills and I start in near darkness at about 6:15. By the time I quit commuting (late October, early November), the whole ride in the morning will be in darkness, perhaps even both directions.

According to the forecast Toronto weather for mornings is about 10C, and about 15C on the return. This is quite reasonable, comfortable weather for riding but it isnt shorts and T shirt weather.
Try a windproof jacket, a long-sleeved jersey/midlayer, some tights/leggings or pants and full gloves rather than fingerless mitts.
The Winter Cycling forum is full of advice but it pays to take advice from people who share your style of winter.

You're right, I am mostly kidding. I barely ride like a maniac in nice weather But ice biking sounds like sooo much fun! And I can avoid the crowded subway. Win-win all around.

You'll get about a million answers from a lot of people who don't actually ride in the cold, so don't take any of this too seriously.

I don't wear anything even remotely cycling specific other than longer, tighter undies to prevent riding up and leg chafing -- that's it. Other than that I wear short and LS t-shrits, a polartec vest, a skull cap or two (I have a shaved head), cargo pants or swishy type jogging pants or jeans, tennis shoes, and I LOVE wool socks.

UNDERDRESS SO THAT YOU DON'T SWEAT -- than you don't need anything to "wick" and stuff you already have works fine.

Cotton is fine for me riding daily 15 miles between 18-105 F (DC 2010 temps I logged). I stopped listening to the "cotton kills" bull**** a few years ago when I noticed that I was one of about 6 riders in the winter around here down from 100's in the Spring/Summer. Theoretical issues with hypothermia don't mean much to me since I commute through an urban area with shelters and homes, and the fact that I'm willing to be cold at first and not sweat. If I took a self guided tour through Greenland I may use more wool, but this isn't realistic for my commute.

Honestly it doesn't matter. Just find what works for you and to hell with everyone else! Including me!

My route to work is mostly in the shade. coming home in the afternoon is not a problem, but the morning commute is really cold on my legs and hands.

have to chuckle. A canadian is asking many of us south of the border to help with winter clothing. right. winter forum is the place to surf.

don't go cheap.
buy cycling specific clothes.
shop around there's a big difference in pricing at shops.
there's no getting around covering your legs.
for the torsoe you need surprisingly little besides a wind block or rain cover of some sort and a decent base layer with a zip up neck.
I use trishorts due to their thin and more comfortable liner
wen you notice your toes getting cold, I recommened thin chemical toes warmers on top of your toes between a sock liner and thin wool sock
for hands I use a similar strategy with a glove liner and then a loose fitting winter glove
regarding actual product suggestions I like: novara headwind pants

Just go to MEC, they have everything you'll ever need for winter cycling.

Interesting, I find the reverse. Because my arms and torso are not doing a lot of work during the ride, they get colder than my legs so I find I can go out in moderate cold (4-10C) with shorts but I need a cycling jacket for the top.

+1.

I really wanted to go for a ride this morning, but it was cold and my sweat pants are too baggy / get caught in gears even with ankle straps.

My solution: pull a pair of my stretchy wicking long underwear over my bike shorts

I'm not sure its something I'd do for a commute. They are black, so from a distance you wouldn't notice the flap on the crotch.

A large portion of my cool/cold weather cycling clothes is actually cross country skiing clothing. Xc skiing gloves, toques, pants, tops, thermal underwear work great for either sport.