The winter weather.
First off, check out in the Internet: you have the easiest and the quickest way to search the winter weather in the city you plan on visiting.
Usually it's rather cold, freezing or below, in the majority areas in Russia in January and February. December is milder. Be prepared to slip on ice and be dusted with snow. Ukraine is warmer.
It can get down to -15 degrees Celsius, give or take 10 degrees during most of the time. And this is considered warm compared to Siberia where you can experience bitter cold.
The way you will survive the Russian winter depends on where you are from and what temps you are used to. Coming from Las Vegas, most countries will feel really cold to you. If you are from Alaska, Russia will seem less freezing.

What to wear in order to survive the Russian winter.
Stock up on warm clothing:
~really warm jacket or a heavy winter coat;
~a shirt and a sweater that you can wear underneath;
~decent fleece lined walking boots;
~thick gloves;
~fleece or flannel lined jeans;
~a fleece or wool scarf;
~a wool hat;
~warm socks.

The piece of advice I can offer:
Dry healthy feet and warm hands help your whole body feel more comfortable; Don't plan on walking for more than an hour without finding a place to warm up.
I would stay away from the clothing you can not take off in a restaurant: if you are going to use layering system you will be too hot.
A warm jacket, a shirt and a sweater that you can wear underneath are enough. When you get to wherever you are going you take off your warm jacket and you are comfortable.
Going to the restaurant with your pretty Russian girl you will be in a taxi usually.
Capital cities have plenty to do. Smaller ones are quiet in winter.
In conclusion, if you don't want to stick out like a tourist wear reserved colours like dark blue, brown or black.

Reminder: there are a lot of beautiful single women in Russia, but you are looking for what's inside, aren't you?

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