I too, am a cheapskate and would rather spend my hard earned money on good beer! I have never owned a pair of winter specific shoes and have done fine over 11 years of Pa winters riding down into single digit land, for the most part, fairly comfortably. I have tried booties, Toe Covers, neoprene socks, Gore-Tex socks, plastic bags, heater packs, duct tape, etc and have found for me the best bet to be, Thick wool socks w/a heater pack taped to the top of my toes over the sock. My toes will sometimes get too hot w/this arrangement. I do like to weatherproof my shoes w/some Camp Dry to help keep the toe area from getting wet. If it's not super cold, I like my neoprene socks over thin bike socks.
For gloves, I like thin, insulated hunting gloves w/a Windstopper layer in them. An extra pair is nice if you are doing a longer ride because your gloves will get wet w/sweat. Thick skiing gloves are a disaster for me because my hands sweat so much.
For clothes, wicking is key. I like a long sleeve jersey with a short sleeved jersey over it and followed up w/a windbreaker. For the legs, I do shorts and leg armour.
For my head, I have a super thin balaklava made from Thinsulate that is awesome! No bunching or getting too hot.
Best thing to keep in mind, if you are warm in the parking lot before a ride, you are over dressed. A thin fleece sweatshirt is nice to have w/you tied onto your CamelBak if you get cold later on or have to stop to change a flat or some other mechanical. Hope this helps!