I think your wardrobe depends alot on what you want to look like ... In other words, how important is it to you to look like a roadie biker. The second question is how long do you expect your rides to take. I find that for rides of one hour or less, there are lots and lots of clothing options. Even up to 90 minutes doesn't require heavy duty (and highly priced) technical clothing. I do appreciate the nicer stuff when I'm off for an entire morning, afternoon or (if I'm really lucky) a whole day.
Around here when it's 40-50 degrees I like any wicking base layer (off some clearance rack and even Target clothes have gotten pretty good lately!) an old wool vest or sweater and a windbreak kind of jacket. I like to wear knickers and wool knee socks. I cover my head and ears with a buff and wear some full finger gloves and I'm good to go.
In the 50s, I just like a wicking T and a wind layer. Maybe long finger gloves ... and I'm fine after 10 minutes.
In the 30s, I go for the above, but make sure they are full sleeve items, leggings, warmer gloves, better ear covering, maybe a light fleece hat and usually my jacket is the Lands End Marinac (they made yellow one year and no one bought them so they had 'em on close outs!) ... It's warm and windproofish. Very cozy and really serves me as my warmest biking jacket down into the 20s. Sometimes I wear it with just a baselayer. You don't go below 30 in Texas, do you?
To be honest, I don't bike under 20 degrees. I find the additional breeze from riding just too brisk. I just walk though ... it's much warmer.
My list of cold weather essentials would be:
2 wicking long sleeve shirts
1 wool vest
1 wool sweater
2 pr knickers (I like the Nashbar brand just fine)
2 pr wool knee-his
long finger biking gloves
warm gloves
1 ear wrap
1 buff (can double around your neck & chin when really cold)
1 fleece hat (tight fitting for under the helmet)
1 windbreaker jacket (like this: http://www.nashbar.com/profile.cfm?c...3A%20Outerwear
1 windblock fleece jacket (e.g.: http://www.landsend.com/cd/ov/prod/0...&CM_MERCH=SRCH
If I didn't bike in under 40 degree weather, I would not get the fleece jacket ... just the windbreak and layer under it.
Good Luck and remember I'm in Chicago!! YMMV.
Campmor also has good prices sometimes on closeouts.



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