my dd is 11 months, so i feel your pain! it takes a little practice, but i feel much more comfortable now than i did a couple months ago. we have a different routine for the 2-3 places we go on a regular basis, since different circumstances call for different strategies.Â
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short trips to the grocery store etc: these are local, on low speed roads, and since we live in an apartment with street parking, generally call for a fair amount of exposure to cold (long walk through the parking lot, or finding street parking, wait outside while i load and unload the groceries, walking between stores). in this case, i do dress her in a down snowsuit... groceries and short errands are already frustrating enough without worrying about being warm enough, and this way i can put her in an unheated car in between stops.
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playdates, malls etc: longer drives on the highway and little time spent outside, we have a one piece fleece suit i sometimes put my dd in, but until it got super cold this week (below -20 for a few days in a row) i just dressed her in warm layers (tights, pants and socks, onesie and sweater) and took her out to the car wrapped in a fleece blanket. i bring the blanket from the house because it will be cold if left in the car.
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walks, trips on public transit etc: we use a carrier under a babywearing coat (lent by a friend, but i will definitely be buying one for my next baby, as it converts from maternity to babywearing to regular). we might also use the snowsuit in the stroller, and i have a carrier cover i made for chilly but not frigid temps that i can use.
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it's not practical for me to heat the car before getting in. we have street parking, so i have to leave the baby in the apartment, run down the block, turn my car on, run back up the block, up three flights of stairs, wrap the baby up, run back downstairs and down the block, all before someone steals my car. on super cold days, we usually don't go anywhere or take public transit. i am concerned about the compression risk of snowsuits in carseats too, but i have decided it's a risk i'm comfortable with on low-speed local roads.