'Cuz I am a man, what wears pants - I'll smoke a churchill and laugh at the weather....
Cold, wind, no sun - no cigar.
Cold (~ 30'f, sub 40'f), no wind, sunny - any perla or minuto
Cold (40'f+ ), no wind, sunny - opens up sizes just a little bit.
I've a little corner in the back of my house that gets the sun in the winter and can help block the breeze, so I can go slightly larger, but won't go past enjoyment to reach smoke just to smoke.