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[Way out of season] Coat suggestions for Chicago winters?

Syalam

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I just moved to Chicago, and the coldest place I've ever lived up to now has been Portland OR (below freezing maybe 3 days a year). I'm soliciting suggestions for a winter coat that will get me through a Chicago winter without hibernating at home. A few specifications:

1. Much as I love tailored clothing (and in fact do own a wool topocoat that goes down close to the knees), I have committed to bike commuting. The coat needs to give me enough freedom of movement (legs and upper body) to ride a bike.

2. Related to (1) - I'd probably want something with a more workwear, classic, or urban aesthetic, rather than tailored coats (so no topcoats, car coats, or maybe even peacoats). Things I've liked the look of include: quilted Barbour coats like the Liddesdale and simply designed, unadorned flight jackets with fur/faux fur lining

3. I'm trying not to break the bank - so suggestions of where to find off season sales, how to wait/shop, or of less popular but still reliable brands are more than welcome. Budget is around $300, maybe with a a bit of wiggle room

4. Last thing - any other suggestions for how to survive the winter (gloves, headgear, legs, boots, etc. are all welcome)

EDIT: Is layering with puffy down jackets underneath a (tailored) outer layer still a thing? Was it ever a thing?
 

breakaway01

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How far is your bike commute and are you going to ride regardless of weather? If the answer to the latter is yes, you have to layer with a wind/waterproof shell on top and bottom. It's going to be hard to look elegant on a bike in a Chicago winter. Down is warm but fleece is easier to take care of if you're going to be sweating into your clothes. Will you be able to change clothes at work?
 

comrade

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I lived in Chicago for 17 years during the 70s and 80s.

1. Don't bike commute unless it is a very short trip.
The weather, along with Chicago drivers and terrible traffic,
is a deadly combination.

2. In grad school I wore down jackets and knit caps.
3. Working I wore tailored clothing some of it very heavy:
British Warm, Invertere greatcoat, Burberry Wool/cashmere
Balmacaan.
I am not particularly sensitive to the cold.
 

Syalam

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My commute is actually pretty short - less than 3mi. I can take it pretty easy, so I won't be sweating too hard. My idea is to maybe have an insulating midlayer (down of some sort?), and then a reasonably waterproof coat. I'm also hoping the coat will serve double duty as a more casual alternative to a tailored coat, and will also be my primary means of staying warm on the really cold days when a regular wool coat might not cut it. Since I don't think I'll be riding more than a few miles at a time during the winter, I'm trying to stay away from a dedicated waterproof jacket that's only for cycling that I won't be able to wear casually.
 

breakaway01

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I wouldn't look for an outer layer that is warm enough to be your 'primary means of staying warm on the really cold days when a regular wool coat might not cut it'. This will be too warm for all but the coldest days. There will be plenty of 30F winter days in Chicago with cars throwing salty slush at you when you will want something waterproof and easy to clean. Arc'teryx Veilance and Nanamica have some outerwear pieces that look good but don't scream 'technical'.
 

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