To keep rain/snow off my glasses, I wear a ballcap. For additional warmth I wear an army-issue Polartec fleece beanie. If more warmth is needed, I'll raise the hood on my jacket/parka or hoodie. I bicycle to & from work every day, regardless of weather. I'm from the Chicago 'burbs and learned early how to dress for winter.

Layers, layers, layers...

Merion wool buff. Most of the time around my neck or in my pocket, but will sometimes be pulled over my head. Either to augment my other hat or as my sole hat.

Wool cap.

And a good hood on my outer shell jacket.

These three go on and off all the time, alone or in combination, responding to changes in wind, temperature, precipitation/snow drift and if I need to cool down a little.

i) Laksen Knitted CTX wool hat.

http://www.swillingtonshootingsupplies.co.uk/store/product/8229/Laksen-knitted-Ctx-hat/

ii) Secolux Ventile® All Weather Cap.

http://www.secolux.co.uk/ventile-all-weather-cap.html


iii) Berghaus Goretex XCR Mountain Cap.

http://www.amazon.co.uk/Berghaus-Mens-Mountain-Gore-Tex-Lined/dp/B004BX8W8Y

Depending on the weather and conditions.

+ 1 on the Tilley winter hat. To get longer life out of it, add a set of the behind the head earmuffs to the ear flaps.

EMS fleece watch cap, double layer.

I have been doing really well with just basic and cheap poly beanies. Nothing fancy except for the ones I buy with brands logos i desire. But in all honesty I am only using them in the teen temps and I am generally highly active outdoors. Very little standing around or walking.

Bringing this old thread to life just to keep the Tilley hats all in one place.

Just in -- TBC1 Tec-wool Ball Cap
It's a typical ball cap but the material is mostly wool and it has ear flaps. I take a walk each morning with the dog and on days like we've had recently I wear a ball cap under a fleece hoodie (If it's raining, the rain coat hood is over that. The ball cap keeps the hoodie up where it belongs rather than covering my eyes. When I saw the Tilley ball cap it was instinctive and automatic. Next thing I knew Tilley had sent me an email confirming the order; they ship very fast.

Needless to say, it's on my head and very comfortable. I haven't tried the ear flaps yet, but I'm sure they work.

PS: Edit to add that I wore the Tilley ball cap on my morning walk, cold and wet from a T-storm last night. It's definitely warmer than the poly-cotton cap I have been wearing. Not as warm as one of my OR Wind Warrior (pg 1 of this thread), but warm for a ball cap. I still haven't used the ear flaps though and those may bring it closer to the OR WW beanie, but that's built for much colder climates than SOCAL.

Here is my cold weather hat:

https://www.varusteleka.fi/pictures/3381357d7e6c14d154.jpg

https://www.varusteleka.fi/pictures/3381357d7e6c0de395.jpg

Outer fabric 70/30 polyester/cotton. Fleece-lining.

That's virtually the same hat I wore in Korea ("frozen Chosen") when I was in the military a looong time ago. Really good headgear for low temps...

The "frozen Chosen" hat looks a lot like the Russian ushanka fur hat. The ushanka may be big, but it's definitely warm. There is a reason that people in such a cold country wear it!