>waterproof jacket and winter tights with overshoes be okay
Pretty much what I've always done, 'cept I normally use a fleecy/roubaix long-sleeve jersey when it gets cold, with or without base layer, and expect/hope to be no worse than warm/wet !
Tights come in a few flavours - like long (bib)shorts, mebbe in heavier lycra; or with roubaix/fleecy lining; and variations of the previous two with a windstopper/windtex (ie windproof) layer, mainly on the front.
I usually go from shorts>roubaix tights, and put up with being a little too warm on occasion- I've got lycra tights too but they tend to get used less.
Another option is leg/knee (arm?) warmers - again, in lycra or roubaix, and/or windproof - handy if say you start your journey at one temperature and finish at another, or the weather changes drastically.
It's rare on an upright for me to need anything other than roubaix tights when it's cold/wet, if you're cycling with a reasonable effort you generate a fair bit of heat and the fleecy stuff keeps you warm, even if you get a bit soggy. Often just a decent base layer under a short sleeve jersey is sufficient to be warm - layering's good and gives you options to warm up/cool down.
When the weather's really cold I wear neoprene socks (eg sealskinz, porelles) as well as overshoes, but that's not often.
Baselayers..hmm, they vary a bit, mebbe one else has some recommendations. My (18yrs old?) Helly Hansen is my favourite under a SS jersey and whilst warm when it's chilly is open enough to not cook too much if it warms up - but their modern (thin) equivalent (unless they've a better alternative) is too thin and don't offer as much insulation. Merino wool is good but can be a little itchy/££, but sometimes you see it on sale (I bought a Technicals jobbie in a sale at Blacks last year)- doesn't get smelly long-term like synthetics either.
Just thought - some tights don't come with a pad insert (probably with a thicker/double layer of material), you may find that's enough (which I do) or you may want a decent pad instead. I guess some people might wear padded shorts under padless tights too.
