When do we start wearing fall/winter boots? Tights?

[kplondon]

Is it a temperature thing? Is it a time-of-year thing? Can you wear boots after September 1 (October 1?) no matter what, or does the temperature also have to be below a certain threshold? Or should you just wear boots and/or tights whenever you would wear a fall/winter jacket?

I'm the other kind of North American

I would be in opaques & boots now if I could get them on.... as it is, only wearing fitflops cos of bad SPD. Just too sore to bend down to put on tights/socks. Don't think boots would zip up anyhow with swollen ankles. Very of all of you in tights & boots already. Dunno how I'll last til mid-October in fitflops....feet are freezing already :(