“I hike naked comfortably for hours at a time with the temperatures in the low to mid thirties F and light breeze, as long as I am moving. If I stop for more than a few minutes, out comes some layers to put on.
The deal breaker under these conditions is the wind. As the temperature goes lower, I tolerate less wind, higher and I can tolerate more of it. I am good for an all day naked hike under most circumstances if the temperature is in the mid fifties or higher. If the wind is light, fifties is fine for me sitting naked, as well.
I have hiked many times before under the same conditions, with various combinations of clothing, and been far less comfortable, sometimes down right miserable. I once started out on a cold overcast day last fall on Mt Monadnock in NH wearing kilt, tank, tee, and knit cap. Within 10 minutes, I was sweaty, cold, and miserable. Off came everything except the shoes and socks, and I was comfy the rest of the day.
Of course, there were plenty of muggles and a stiff breeze on the summit, so I put the clothes back on till after I had started back down. The temperature that morning was 38 deg F with a moderate breeze, and did not get out of the 40s the entire day. I will jump at the chance to hike naked in the rain in 50 deg F anytime that I can. I will never do it again textile if I can avoid it.
. . . Though I did not say it, I was implying that one ease in slowly, by continuing to hike naked through the fall and into the early winter, and listen to one's body. Put on clothes or retreat when it is no longer enjoyable.
Hiking naked in the cold is best done with a pack. The only difference between textile hiking in the cold and naked hiking in the cold is that everything that you would be wearing textile, and then some, plus a survival kit, will be in your pack in case you need it.
Cut back your mileage, and know your area, as the days are short. Also keep in mind that when hiking naked in the cold you must eat and drink, almost continuously. Your body is probably burning more calories than usual and may crash suddenly if low on nutrition and hydration. The possibility of hypothermia is not to be taken lightly.
Done with care, hiking naked in the off season is a most amazing experience. Sorry, this has little to do with losing shame, but consider the possibility of encountering a textile hiker while hiking naked on a typical late fall-early winter or late winter-early spring day! The contrast in attire or lack there-of is a conversation starter to put it mildly. Mutual respect and quiet confidence goes a long way in these situations. As usual, I don't go out there to create these situations, but I have been there on occasion, and the experiences have been rich. More naked-textile casual encounters in varied, but appropriate settings - good thing." – Dan