I'm usually only walking from my car into a store, etc., so am not out in the cold for any great length of time. My jacket has a hood, and I just put it on before I get out of the car, take it off when I get inside. I specifically look for jackets w/hood, so this must be my sub conscious telling me it's what I like. ;o)

I have a selection of knit hats that I made. And I have the fleece earmuffs that are like a head band. When it's cold and I'm going to be walking or shoveling for a long time, I wear both the headband and then the knit hat.

Re hoodies...just be sure to take your hoodie off before you start driving. One night, I forgot and couldn't see behind me and drove my car into another one of my cars. Not a good thing!

Carhardt fleece-lined knit; colorful Norwegian knitted wool hat with ear flaps and bobble on the point on top; assorted hand knit "tube-type" hats that fold up (or down) in layers over my ears; a couple of LL Bean fleece hats in various colors (not very warm in any breeze, so mostly I sleep in them in my unheated bedroom); army-surplus wool balaclava; a faux-suede rounded cap with luxe faux-fur trim ring all around (this is my "dress-up" hat worn with my wool top coat in the city.) Also my down jacket has a hood which I can pull up and cinch closed in extreme weather when driving the tractor on the farm.

I need a hat when I first go out in the winter, but usually I am working too hard to want anything on my head, even in single digit or below zero temps. I am dressed like an Eskimo, but bareheaded except during storms or really windy conditions. I like to get as much sun as I can on my face during the winter to make some Vit D. since little else is exposed around here for 5 or 6 months. (Though during a warm January or Februry thaw, I've been known to go outside in just camisole and panties for as long as I can stand it, just to soak up some sun rays.)

BTW, if you have ugly, but warm, knitted hats (and scarves and mismatched gloves & mittens, etc.) don't dispose of them. Make up a little package of them and stow it in the pocket behind your car seat in every vehicle. If you were stranded, or needed extras in an emergency, they'd be readily available and under those circs. better warm that fashion-correct.

L.

Wool berets. They don't smash your hair down flat like some hats. They can be rolled up and bunched in your pocket. On warmer days, you can wear them like a jaunty beret. On colder days you can pull them down over your ears. If you have long hair, you can tuck it all up under the beret and it doesn't get tangled by the wind.

I am not a hat person, never have been though I think they are cute on others. When I run in cold weather, I wear this fleece ear warmer. Though I don't worry about it ruining my hairdo b/c I wash my hair anyway after I run, it would be perfect for someone who doesn't want to deal with static or smushing one's 'do. It keeps my ears very warm!

http://www.thenorthface.com/webapp/wcs/stores/servlet/ProductDisplay?productId=120860&storeId=207&catalogId=10201&langId=-1&from=subCat&parent_category_rn=11724&variationId=128

I have two go-to warm hats.One is a fleece that I pull down over my ears when I'll be outside for awhile, usually walking or shoveling snow (noooo!). It keeps my ears nice and warm but does make a mess of my hair. The second is a warm hat but not fleece or knit. It fits closely to the top of my head but had a soft brim. This one does not mess up my hair and looks less outdoorsy. I also have some head bands but I don't like them all that much. They slide up and then my hair looks like the top of a muffin. I can't stand those ear muffs that go around the back of your head. They are so annoying. I used to have some Swix ear muffs which I loved because they were warm and don't squash your hair. Either I keep losing them or others are borrowing them from my box of hats!

Here is a link that might be useful: swix

Hated wearing hats when we lived in the Northeast ... luckily don't have much need for hats now that we live in CA.

Even when skiing I only wear a fleece head band 99% of the time. Did I mention that I hate hats! If it is really cold then I'll pull up the hood on my ski jacket over the headband.

Arc'teryx beanies are windproof and warm. You do get beanie hair. However I've found that just wearing my arc'teryx gaiter and my headband is warm enough.

Got a very cut "snood" style hat last month at Polo outlet. It is knit, with a bit of sparkle, and is best described as a stretched out beret, but knit.

The band in warmer weather sits on you head where you would have a head band. And the hat just hangs back kind of loosely.

In colder weather you can wear it more forward on your head, with the band covering your ears.

Your hair can be tucked up inside if it is windy.
Doesn't give you hat head.

The other hat I like is felted wool with a felt flower, and covers your ears. I got at Nordstrom a few years ago. Cute and not so tight that you get hat head

I am a person who feels the cold, and I usually will wear a hat at the end of the work day when I get in that cold car for the drive home.

For exercising in the cold I have a knit ski hat with a fleece lining over your ears. That is nice because the fleece keeps your ears warm, and the knit allows some cooling air to get in when you are exercising and warm up a bit.

I will also add that I got a Lands End Squall long coat a few years ago just to wear for winter walking. It is fantastic. Down to the knees so covers your entire rump which can get cold even when walking. Breaks the wind. 2 way zipper. I look like a mail man, but it is great for walking when it is cold.