We mostly work skyclad, however it's usually indoors by a close lit fire, however can get quite cold before we're summoned in. When working outdoors, both due to the weather and also the possibility of passer-byers, we do have robes that we were required to make ourselves, and there are also times where those will wear other items indoors as well due to say medical reasons, that time of month for the females, e.t.c...
I've seen quite a few sources indicating historic healers, charmers, witches, cunningfolk, e.t.c. would do their workings and spells mostly inside their own homes when approached,or in the home of the person they were working for. Often those living in cottages of the woods on the outskirts of the community were said to get their 'powers' from outdoor settings like fairy raths, but all are said to be in normal dress attire. I was always under the impression our robes were kind of a western ceremonial thing. Crowley explains it well in Book 4(ABA), and Sanders got it from Hermetic sources.
I think it was a creation of the peoples' minds during the inquisitions that conjured up images of getting naked, and what mostly happened and 'Witches Sabbats' probably in rebellion of the religious and moral restraints on society at he time to act out their human nature. I think it was a combination of this, and what was supposedly said about the Witches of Thessaly that had to do with its later incorporation into Wicca either by an occult group like the Rosicrucian Fellowship of the New Forest trying to reconstruct Murray's hypothesis, or Gardner being influenced by Leland's writings that had to do with the skyclad thing. (He was a naturist, and naturists still meet today at the club in Hertfordshire his Bricketwood coven met at) Whether or not it was a legit practice of Italian witches I guess will never be known. They sure get better weather than here in the British Isles!