I know there are probably as many ways as there are glove models, but it would be interesting to hear about the different methods that glovers use to break in a glove.
I guess we would need to clarify 1)infield/outfield, 2)old school leather v. comtemporary
anything else?
My 1st Rawlings Made in USA Horween leather Pro-T (outfield glove) that I bought in 1984 (CEO01) took me about 3 months to break in. It was hard as a rock. I put it in a hot car for about an hour to warm up the leather to open up the pores. I didn't want it to get too heavy so I only lightly coated it with Rawlings Glovolium.
I applied a few coats of it in the pocket area just to get it started. I would try and play catch with it as much as possible but when I couldn't find anyone to play catch with, I kept pounding my fist into the pocket and I would knead the leather while watching tv.
Eventually it formed a nice thumb-to-ring finger break and pocket just by playing catch and using it during practice. I didn't know about the other types of oils and creams that were available back then, but would probably have used vaseline, Lexol or lanolin.
I have never applied anything else to the glove since 1994 and the glove is still very light, nicely conditioned with only about a 1/8" of checking at the hand opening from perspiration (I should have worn a batting glove?).
The pocket closes naturally and the fingers are still firm.