Chazal tell us that any home where wine does not spill like water had no Bracha in it. The Rema writes (OC 296:1) that by Havdala Motza'ei Shabbos, in middle of making the Bracha Borei Pri HaGafen, you should tip your Kos and spill out some wine. The Mishna Brura writes that our Minhag is not to spill wine in middle of the bracha but when pouring the kos before Havdala, to pour more than the Kos holds and spill a bit, but not too much since it is wasteful.
The Rema also says that we pour wine from the Kos onto the Havdala candle to extinguish it. Then we wash our face with the wine to show how much we love the mitzva. The Minhag Yisroel Torah brings from the Kitzur Shela that we should say the pasuk "Mitzvos Hashem Bara Meiras Eiynayim" when we do this. The Chasam Sofer says that his father's minhag was to also put some of the wine on his forehead.
What about the famous pockets? He brings from the Toldos Shmuel that although many of the Hamon Am put wine on their pockets, he does not know the Mekor nor has he seen the "Midakdikim" do this. The Minhag Yisroel Torah says that although he also did not find any source for this minhag, it is known that Midakdikim do it, including the son of the Likutei Maharich.
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