I light the log-burner, crack open the brandy/red wine/southern comfort and watch an old film.
Now that is class and 100% pure style.
I work with 3 others and they just wear whatever. During the summer I spend a few bob on proper winter clothing.
Last winter, as with previous winters, I did not once suffer from the cold. The others I work with found it a big problem.
I think it pays to have proper decent winter clothing. You also have to think of the years to come when when todays cold joints for days on end will matter.
This summer I bought 3 sets of untrendy thermals. I paid £180 for them but they are for mountain climbing in sub zero temperatures. One thing about buying stuff that is for climbers is that such clothing means that you can move freely and still be warm. Layers of clothes can become very restrictive and tiring.
For boots, anything Gore-Tex. 100% waterproof in any conditions.