I don't spend high $$; what works form me:
Basic shoe covers and wool socks (DeFeet Wollie Boolies); I have a pair of fleece-lined tights (Louis Garneau). I use a wool base layer (Endura), my regular jersey, and a Louis Garneau "Course" rain/wind jacket (usually with thin arm warmers on underneath for layering). If below 35 degrees I use a Louis Garneau neck gaiter, which I can use to breath through in very cold weather. Good winter gloves (BioRacer) was my biggest splurge. And, of course, some sort of fleece cycling cap. Most of this I got from my LBS. I can mix/match layers for anything form 20F on up. Honestly, above 40 degrees I'll ditch the jacket and just us a layer of newspaper under the jersey to block the wind; which I can dispose of easily if it warms to 50