Okay I have a question. I read on some winter biking site that for winter wear a proper layering strategy is for three layers - a wicking layer, an insulation layer, and a wind breaking layer.

This is my first winter  using a layered approach so I am wondering what you all do.

So far I have been using a two layer approach.  An Android II soft shell which is a good bit thicker than a windbreaker (which others suggest) and a wicking layer that is designed for cold weather (typically a thermal jersey or Nike/Underarmor winter jersey). 

This approach has been working down to 30 degrees but  under thirty I am chilled for the first 10-15 minutes using this approach.  I have a 40 minute commute so I warm up okay for most of the ride but it still is a bit uncomfortable at the beginning.  I am considering adding the insulation layer on the colder days but am worried about overheating.

For you winter  riders I'm curious how many layers you ride with on the colder days and do you over/under heat sometimes?  Perhaps I just have to get used to being chilled for 10-15 mins.

J

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Being a little chilled for the first 10-15 minutes is exactly the right amount of clothing. My commute is much shorter than yours, so I am in the elements for a much shorter period of time and have more flexibility in what I wear. On longer rides (>1 hour) in cold weather (below 25), I wear (1) wicking, (2) insulation, (3) wind/waterproof shell on top; (1) wicking/insulation, (2) wind/waterproof on the bottom.

Being cold at first is best, as long as you know you've dressed appropriately. I keep the vents in my outter later closed for the first ten minutes. That helps me get warmed up faster. I try to open the pit vents and rear vents in my jacket before I'm hot.

Arm warmers and scarfs are very handy for extra warmth if you don't want to commit to another full layer. I had a full zipper added to my warmest long sleeve wool jersey by a seamstress, this also helps let out extra heat when you've overdressed.

thank you both for your suggestions. I'll tolerate the chill then at the beginning.  

Ditto. I do both of these all the time. I generally do a long-sleeved wicking layer under my wind/waterproof shell. I keep my pit zips closed for the first 1.5mi, then vent as needed. If I'm really warm, I'll crack my main zipper a bit too or maybe remove the buff/scarf around my neck. I've basically got it down to a science at this point, so I can aim for certain long lights (Diversey/Western/Elston or Elston/Fullerton/Damen) as "adjustment points" en route.

Kelvin Mulcky said:

 I try to open the pit vents and rear vents in my jacket before I'm hot.

Arm warmers and scarfs are very handy for extra warmth if you don't want to commit to another full layer. 

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