DEERLORD Just out of curiosity, do you use the liquid Redwing boot oil for your boots? That's the stuff my local shoe shop owner (who happens to be a Redwing dealer) recommended (and sold) to me back when an old pair of Bates needed to be rehydrated after a week of constant soaking. It works very well but I don't find it to smell particularly pleasant (not particularly unpleasant either, just not something I would want to smell all the time). It does work a charm though, and it's easy to apply, which will probably keep me coming back when I need more boot oil. To the O.P. As far as oiling, you can generally tell when the leather needs some love pretty easily. Don't let it get as far as abrasion or cracking due to dryness. I find that I can usually sense a difference in how the leather around my toe area where the boot bends to walk. If you'd prefer, just feel the leather every three or four weeks and when it starts feeling stiff and dry give it a little bit of conditioner. According to the aforementioned boot oil bottle, Redwing recommends reconditioning "at least once a month". I find my boots don't need it that frequently. YMMV. Hope this helps!