Re: 16th - 17th century sailors: stockings and shoes - YES!
It was probable that they would have known of the antiseptic qualities of pine oil though not knowing about the nature of its curative powers. Most ships had a medicine or herbal chest of sorts and some things were known by different names like Lockjaw for Tetanus. The works of Galen, Avicenna and others were starting to be rediscovered in this period so modern medicine was in its very early stages. Sailors would have probably known of the curative powers of shark liver oil and other things readily available from the sea.
It is a good idea to look at contemporary paintings( and van deVelde is very good) rather than reflecting. Often hose and stockings would have reinforced soles though it is likely that sailors would take their hose, stockings and shoes off in their rest periods to prevent foot root and to apply barriers eg goose fat, whale oil or fish oil etc . The other side of not wearing stockings or shoes is for the feet to get fungal or viral infections(because of the confined nature of the accommodation ) or wear them too much and get foot rot. Funny how soldiers in the trenches in 1914-18 had to relearn this.
How oi los mi leg? Norra Spanyards shart but oi got a splinner in Devoport choppin kindling.
Sorry, the old Plymouth Dome by the Hoe use to have an actor doing an Elizabethan sea dog for the visitors. He did it so often that he was convinced he knew more than the real Elizabethans- and in truth he probably did.