Living where I do, I have rarely experienced any outside temp lower than about 46F, even in the dead of "winter." But I can attest to optimum environmental ambience adding exponential pleasure to a fine cigar. I will avoid smoking if I feel the least bit of discomfort from the weather or if I have a cold that blocks my ability to accurately sense aromas, because both those factors could override the enjoyment of something I paid eight, ten, twelve or more dollars to enjoy - a bad cigar experience is not unlike a bad movie theatre experience "What a waste THAT was!"
I have added high wind to my list of "must avoid" environments. I was recently smoking on an ocean-facing, open-side but covered porch of the beach house owned by a friend of mine. After having to go inside to light our cigars, we went outside with drinks to enjoy the acitivities transpiring on the beach below. The whipping wind so normal for oceanfront caused big difficulties in picking up the slightest aromas off the cut, body or even the foot of the expensive cigars I had taken for the holiday visit. Unless I practically stuck a part of the cigar up my nose, the 25 knot sea breeze carried all the good smells away too fast. The best smoking experience for me comes when the smoke lingers in front of me or at least lightly swirls around a bit before being carried off. We could have gone around back to a small courtyard where the wind was blocked, but then would have been in intense 90F+ temps and direct sunlight (another environment in which to NOT enjoy a cigar) nor could have watched anything (or anyone) of interest.
Smoking just to get a cigar smoked seems wasteful and also could suggest a dependency problem, so I try to make sure the surroundings for a smoke are as good as the cigar I am smoking, or I will put off the effort for better times. (Or else smoke a POS that I have been wanting to cull out of my humidor - but how wonderful it that?!! LOL)