I'm a serious cold weather weenie. And my commute only takes me about 15-20 minutes and I freeze my tail off even when it's only in the low 50's.
Someone else posted this website a few days ago. This place has a couple rain jackets for VERY cheap. I just ordered one a few days ago. It hasn't arrived yet, but I'm hoping it'll be a good rain jacket. It's probably cheaper than what you may pay at Walmart, and probably better quality. $11 for a seemingly good jacket is pretty reasonable IMO (but I may get it in the mail and it might be crap).
http://www.blackbottoms.com/BBCW2010...tsAndTops.html
They also have some really cheap shorts on sale, too, and some windproof cycling booties for about $5.
I agree with twin on finding a good, cheap wool sweater (and wool socks) to wear under a rainproof jacket. I found a sweater at goodwill last winter for $3 and it's warmer than my really expensive winter cycling jacket when paired with a lighter windproof shell (and with a giant snowflake on the front- it's kinda pretty, too).I was just at the goodwill last weekend and found 2 pair of ski pants. If I didn't already have nice, warm, waterproof pants- I would have gotten them.
I wear my Keen sandals all winter long, and I have a pair of thick wool socks that keep my toes pretty toasty (and windproof booties help).
For the glasses problem, I don't really know. I have a visor on my commuting helmet, and that helps with some moisture, but not a lot... hopefully someone will have some words of wisdom for that one.




I was just at the goodwill last weekend and found 2 pair of ski pants. If I didn't already have nice, warm, waterproof pants- I would have gotten them.
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