We also walk and take public transportation almost everywhere in a cold northeastern city with lake effect. This is what works for me and my 18mo.
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edited for clarity
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1. I always take one of those thicker "pashmina" type shawls with me no matter what carrier I use. They are good as a rebozo and also as an extra support with a ring sling.
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2. I made a simple babywearing coat with a zip in panel using old navy fleeces. I dress us in light layers and put the coat over us. Last winter, I just wore a big sweater over us and added my shawl wrapped around us like a towel.
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3. If I'm riding the bus more than walking, I take the ring sling. If I'm walking alot, I take a wrap. I leave the ring sling on. I take the wrap off and put it in my backpack, and use my shawl as a rebozo for quick ups and downs inside. If I walk more than expected with the RS, I use the shawl as extra support (going like an X). I have also wrapped loosely on the front to get on the bus. I like having her in a carrier on the bus because I feel it is safer if we were to stop suddenly.
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4. I wrap high and wear a backpack low on my back. As long as the backpack isn't over filled this is quite cozy for the kiddo. I have a ridiculously long size 6 wrap that is on the thinner side and as I've gotten more comfortable with using it, I don't find it to be a pain to carry in my backpack when my toddler is down walking. I will often pack her coat and snow pants in my backpack just in case she wants to walk outside, but she usually doesn't.
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5. A medium length wrap is great too.. Ruck tied in front is a lot more comfy than I thought it would be. I do like the long wrap though because I feel like it is nice and cozy for her. If the weather suddenly turns really bad, I can put her on my front and pull the crosses over her face to protect her.
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6. A SSC is probably great. I have a lightly padded buckle tai that I don't like now that DD is over 20 lbs. But I imagine you could do all the same with the SSC - wear it under a coat and all.
Edited by cyclamen - 12/9/10 at 8:07pm